CH615144A5 - - Google Patents

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Publication number: CH615144A5
Authority: CH; Switzerland
Prior art keywords: formula; methyl; acetal; reaction; acid
Prior art date: 1973-08-16

Application number

CH1120774A

Other languages

German (de)

English (en)

Inventor

Yataro Ichikawa

Teizo Yamaji

Mamoru Yamamoto

Original Assignee

Teijin Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-08-16

Filing date

1974-08-16

Publication date

1980-01-15

1973-08-16 Priority claimed from JP9128073A external-priority patent/JPS5950654B2/ja

1973-10-02 Priority claimed from JP48110179A external-priority patent/JPS5950655B2/ja

1973-10-05 Priority claimed from JP11211473A external-priority patent/JPS5950656B2/ja

1973-11-21 Priority claimed from JP13010973A external-priority patent/JPS5082006A/ja

1974-08-16 Application filed by Teijin Ltd filed Critical Teijin Ltd

1980-01-15 Publication of CH615144A5 publication Critical patent/CH615144A5/de

Links

238000006243 chemical reaction Methods 0.000 claims description 68
125000004432 carbon atom Chemical group C* 0.000 claims description 58
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 40
238000000034 method Methods 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
125000000962 organic group Chemical group 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 15
239000003377 acid catalyst Substances 0.000 claims description 13
125000002723 alicyclic group Chemical group 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 3
230000008030 elimination Effects 0.000 claims description 2
238000003379 elimination reaction Methods 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 171
150000001299 aldehydes Chemical class 0.000 description 87
150000001241 acetals Chemical class 0.000 description 53
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 52
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 42
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 42
238000010521 absorption reaction Methods 0.000 description 40
-1 acetylene alcohols Chemical class 0.000 description 25
239000003054 catalyst Substances 0.000 description 25
238000002329 infrared spectrum Methods 0.000 description 24
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 24
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
229940098779 methanesulfonic acid Drugs 0.000 description 21
150000007524 organic acids Chemical group 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
150000001728 carbonyl compounds Chemical class 0.000 description 18
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 16
WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 16
125000000623 heterocyclic group Chemical group 0.000 description 16
QIACXWLIFNNZDL-UHFFFAOYSA-N 4,4-diethoxy-2-methylbut-1-ene Chemical compound CCOC(CC(C)=C)OCC QIACXWLIFNNZDL-UHFFFAOYSA-N 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
150000002148 esters Chemical class 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229940043350 citral Drugs 0.000 description 12
230000002378 acidificating effect Effects 0.000 description 11
239000000047 product Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 7
229910052921 ammonium sulfate Inorganic materials 0.000 description 7
235000011130 ammonium sulphate Nutrition 0.000 description 7
238000004821 distillation Methods 0.000 description 7
239000007791 liquid phase Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
235000006408 oxalic acid Nutrition 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
239000002904 solvent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
238000005755 formation reaction Methods 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 5
239000005711 Benzoic acid Substances 0.000 description 4
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
235000010233 benzoic acid Nutrition 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000012295 chemical reaction liquid Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
OHCMANJUZNNOQW-UHFFFAOYSA-N 2,4,4-trimethylcyclohexene-1-carbaldehyde Chemical compound CC1=C(C=O)CCC(C)(C)C1 OHCMANJUZNNOQW-UHFFFAOYSA-N 0.000 description 3
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 3
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
GKTYXDFHEKQLPJ-UHFFFAOYSA-N 3-methylocta-2,6-dienal Chemical compound CC=CCCC(C)=CC=O GKTYXDFHEKQLPJ-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
125000003158 alcohol group Chemical group 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
230000008707 rearrangement Effects 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000011973 solid acid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
238000005979 thermal decomposition reaction Methods 0.000 description 3
239000012808 vapor phase Substances 0.000 description 3
CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 description 2
239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 2
YKXLOLXPAVQFLX-UHFFFAOYSA-N 3,7-dimethylocta-2,6-dienal Chemical compound CC(C)=CCCC(C)=CC=O.CC(C)=CCCC(C)=CC=O YKXLOLXPAVQFLX-UHFFFAOYSA-N 0.000 description 2
SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 description 2
SNCXDXXJGCFMIG-UHFFFAOYSA-N 7-methyl-4-phenylocta-2,6-dienal Chemical compound CC(C)=CCC(C=CC=O)C1=CC=CC=C1 SNCXDXXJGCFMIG-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229940043259 farnesol Drugs 0.000 description 2
229930002886 farnesol Natural products 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 2
239000011592 zinc chloride Substances 0.000 description 2
235000005074 zinc chloride Nutrition 0.000 description 2
MCHNNYCNFSGSIS-UHFFFAOYSA-N (1-acetyloxy-3-methylbut-3-enyl) acetate Chemical compound CC(=C)CC(OC(C)=O)OC(C)=O MCHNNYCNFSGSIS-UHFFFAOYSA-N 0.000 description 1
AVHRJMXIKKJVHG-QIRCYJPOSA-N (2E,6E,10E)-geranylgeranial Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\C=O AVHRJMXIKKJVHG-QIRCYJPOSA-N 0.000 description 1
239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
NZUZZMAREFZHLJ-UHFFFAOYSA-N 1,1-bis(3-methylbut-2-enoxy)oct-3-ene Chemical compound CCCCC=CCC(OCC=C(C)C)OCC=C(C)C NZUZZMAREFZHLJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
OQJWBWUEDSZTOY-UHFFFAOYSA-N 2,6-dimethylhepta-2,6-dienal Chemical compound CC(=C)CCC=C(C)C=O OQJWBWUEDSZTOY-UHFFFAOYSA-N 0.000 description 1
XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 description 1
FKTLISWEAOSVBS-UHFFFAOYSA-N 2-prop-1-en-2-yloxyprop-1-ene Chemical compound CC(=C)OC(C)=C FKTLISWEAOSVBS-UHFFFAOYSA-N 0.000 description 1
XUAWLMBAEKLIBF-UHFFFAOYSA-N 3,5-dimethylhepta-2,6-dienal Chemical compound C=CC(C)CC(C)=CC=O XUAWLMBAEKLIBF-UHFFFAOYSA-N 0.000 description 1
KZKMQXXAIXEAFR-UHFFFAOYSA-N 3,6-dimethylhepta-2,6-dienal Chemical compound CC(=C)CCC(C)=CC=O KZKMQXXAIXEAFR-UHFFFAOYSA-N 0.000 description 1
PEAPMUZNABIRAP-UHFFFAOYSA-N 3,6-dimethylocta-2,6-dienal Chemical compound CC=C(C)CCC(C)=CC=O PEAPMUZNABIRAP-UHFFFAOYSA-N 0.000 description 1
IGCMALGJSKSLLP-UHFFFAOYSA-N 3-methyl-1-[1-(3-methylbut-2-enoxy)but-3-enoxy]but-2-ene Chemical compound CC(C)=CCOC(CC=C)OCC=C(C)C IGCMALGJSKSLLP-UHFFFAOYSA-N 0.000 description 1
JXJJROZNPSPULL-UHFFFAOYSA-N 3-methyl-4,4-bis(2-methylprop-2-enoxy)but-1-ene Chemical compound CC(=C)COC(C(C=C)C)OCC(C)=C JXJJROZNPSPULL-UHFFFAOYSA-N 0.000 description 1
REAMCSFHUFZAHX-UHFFFAOYSA-N 3-methylhepta-2,6-dienal Chemical compound O=CC=C(C)CCC=C REAMCSFHUFZAHX-UHFFFAOYSA-N 0.000 description 1
CZWWCTHQXBMHDA-UHFFFAOYSA-N 3h-1,3-thiazol-2-one Chemical compound OC1=NC=CS1 CZWWCTHQXBMHDA-UHFFFAOYSA-N 0.000 description 1
SPALDLRFLIGRGY-UHFFFAOYSA-N 4,4-bis(3-methylbut-2-enoxy)but-1-enylbenzene Chemical compound CC(C)=CCOC(OCC=C(C)C)CC=CC1=CC=CC=C1 SPALDLRFLIGRGY-UHFFFAOYSA-N 0.000 description 1
WPYUMMKMKKAABW-UHFFFAOYSA-N 4,4-bis(but-3-en-2-yloxy)-2-methylbut-1-ene Chemical compound C=CC(C)OC(CC(C)=C)OC(C)C=C WPYUMMKMKKAABW-UHFFFAOYSA-N 0.000 description 1
BNAKVVACHPNXPC-UHFFFAOYSA-N 4,4-diethoxy-3-methylbut-1-ene Chemical compound CCOC(OCC)C(C)C=C BNAKVVACHPNXPC-UHFFFAOYSA-N 0.000 description 1
PRCYIYOCMALJCX-UHFFFAOYSA-N 4,4-diethoxybut-1-ene Chemical compound CCOC(CC=C)OCC PRCYIYOCMALJCX-UHFFFAOYSA-N 0.000 description 1
HJWJGMBHZDRVHW-UHFFFAOYSA-N 4,4-diethoxybut-1-enylbenzene Chemical compound CCOC(OCC)CC=CC1=CC=CC=C1 HJWJGMBHZDRVHW-UHFFFAOYSA-N 0.000 description 1
YQBLLEKKSCCSJF-UHFFFAOYSA-N 4-ethoxy-2-methyl-4-(3-methylbut-2-enoxy)but-1-ene Chemical compound CCOC(CC(C)=C)OCC=C(C)C YQBLLEKKSCCSJF-UHFFFAOYSA-N 0.000 description 1
MMVUZMIOJNPDME-UHFFFAOYSA-N 4-methylbenzenesulfonate;triethylazanium Chemical compound CC[NH+](CC)CC.CC1=CC=C(S([O-])(=O)=O)C=C1 MMVUZMIOJNPDME-UHFFFAOYSA-N 0.000 description 1
UKKOMONUXJHWME-UHFFFAOYSA-N 5-(2-methylprop-1-enyl)non-2-enal Chemical compound CCCCC(C=C(C)C)CC=CC=O UKKOMONUXJHWME-UHFFFAOYSA-N 0.000 description 1
ZNGDYTQAWYIRTM-UHFFFAOYSA-N 5-(furan-2-yl)-3-methylpentan-2-one Chemical compound CC(=O)C(C)CCC1=CC=CO1 ZNGDYTQAWYIRTM-UHFFFAOYSA-N 0.000 description 1
TYFJTEPDESMEHE-UHFFFAOYSA-N 6,8-dihydroxy-3-[2-(4-methoxyphenyl)ethyl]-3,4-dihydroisochromen-1-one Chemical compound C1=CC(OC)=CC=C1CCC1OC(=O)C2=C(O)C=C(O)C=C2C1 TYFJTEPDESMEHE-UHFFFAOYSA-N 0.000 description 1
DAYOEEGKLUCJMX-UHFFFAOYSA-N 7-methylocta-2,6-dienal Chemical compound CC(C)=CCCC=CC=O DAYOEEGKLUCJMX-UHFFFAOYSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000005792 Geraniol Substances 0.000 description 1
AVHRJMXIKKJVHG-UHFFFAOYSA-N Geranylneral Natural products CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CC=O AVHRJMXIKKJVHG-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910002666 PdCl2 Inorganic materials 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 description 1
235000012550 Pimpinella anisum Nutrition 0.000 description 1
240000004760 Pimpinella anisum Species 0.000 description 1
HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
125000005075 adamantyloxy group Chemical group C12(CC3CC(CC(C1)C3)C2)O* 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
GDCXBZMWKSBSJG-UHFFFAOYSA-N azane;4-methylbenzenesulfonic acid Chemical compound [NH4+].CC1=CC=C(S([O-])(=O)=O)C=C1 GDCXBZMWKSBSJG-UHFFFAOYSA-N 0.000 description 1
239000011324 bead Substances 0.000 description 1
229910052810 boron oxide Inorganic materials 0.000 description 1
MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
229940043232 butyl acetate Drugs 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
229960001826 dimethylphthalate Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
229960002089 ferrous chloride Drugs 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940113087 geraniol Drugs 0.000 description 1
YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
VIAVRWIIHIKOIR-UHFFFAOYSA-N heptane;4-methylbenzenesulfonic acid Chemical compound CCCCCCC.CC1=CC=C(S(O)(=O)=O)C=C1 VIAVRWIIHIKOIR-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical compound CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005608 naphthenic acid group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000005338 nitrobenzoic acids Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000005441 o-toluyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
125000002457 octadec-9-ynoyl group Chemical group C(CCCCCCCC#CCCCCCCCC)(=O)* 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/16—Acetic acid esters of dihydroxylic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

CH1120774A 1973-08-16 1974-08-16 CH615144A5 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP9128073A JPS5950654B2 (ja)	1973-08-16	1973-08-16	不飽和カルボニル化合物の製造法
JP48110179A JPS5950655B2 (ja)	1973-10-02	1973-10-02	不飽和カルボニル化合物の製造法
JP11211473A JPS5950656B2 (ja)	1973-10-05	1973-10-05	不飽和カルボニル化合物の製造法
JP13010973A JPS5082006A (da)	1973-11-21	1973-11-21

Publications (1)

Publication Number	Publication Date
CH615144A5 true CH615144A5 (da)	1980-01-15

Family

ID=27467893

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1120774A CH615144A5 (da)	1973-08-16	1974-08-16

Country Status (10)

Country	Link
US (1)	US4209644A (da)
AU (1)	AU7218574A (da)
BE (1)	BE818839A (da)
BR (1)	BR7406740D0 (da)
CH (1)	CH615144A5 (da)
DE (1)	DE2439140C3 (da)
FR (2)	FR2254545B1 (da)
GB (1)	GB1482614A (da)
IT (1)	IT1019970B (da)
NL (1)	NL7410998A (da)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2926562A1 (de) *	1979-06-30	1981-01-22	Basf Ag	Verfahren zur herstellung von citral
US4347192A (en) *	1979-07-30	1982-08-31	G. D. Searle & Co.	Derivatives of α,β-unsaturated ketones
DE3013672A1 (de) *	1980-04-09	1981-10-15	Consortium für elektrochemische Industrie GmbH, 8000 München	2,4-dialkyl-2.6-heptadienal-derivate, verfahren zu deren herstellung und ihre anwendung als geruchs- und geschmacksstoffe
DE3118656A1 (de) *	1981-05-11	1982-11-25	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von (alpha),ss-ungesaettigten aldehyden und 2,7-dimethyl-2,6-octadienal
US4400550A (en) *	1982-02-12	1983-08-23	Albany International Corp.	Synthesis of the navel orange worm pheromone (Z,Z)-11,13-hexadecadienal
FR2656604B1 (fr) *	1990-01-03	1992-03-20	Rhone Poulenc Sante	Procede de preparation du citral.
US5739100A (en) *	1993-12-17	1998-04-14	Nippon Zeon Co., Ltd.	Cis-3-hexenal-cis-3-hexenyl acetal compound, process for preparing same, and fragrance-or flavor-imparting or fragrance-or flavor-retaining agent and perfume composition containing same
US6087322A (en) *	1997-04-24	2000-07-11	The Procter & Gamble Company	Fragrance pro-accords
DE10012949A1 (de) *	2000-03-16	2001-09-27	Henkel Kgaa	Kieselsäureester-Mischungen
EP2726232A1 (en) *	2011-07-01	2014-05-07	Ask Chemicals L. P.	Compositions prepared from an aldehyde and a furfuryl alcohol and their use as binders
WO2020212164A1 (en) *	2019-04-15	2020-10-22	Dsm Ip Assets B.V.	New process for the production of retinal

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2501144A (en) *	1947-12-19	1950-03-21	Hercules Powder Co Ltd	Unsaturated aldehydes and preparation thereof
US2947786A (en) *	1958-04-14	1960-08-02	Eastman Kodak Co	Substituted unsaturated aldehydes
CH510602A (fr) *	1967-05-26	1971-07-31	Firmenich & Cie	Procédé pour la préparation de composés carbonylés
DE2157035C3 (de) *	1971-11-17	1974-07-04	Basf Ag, 6700 Ludwigshafen	Verfahren zur Herstellung höhermolekularer alpha-beta-ungesättigter Aldehyde
US4016212A (en) *	1973-03-12	1977-04-05	Hoffmann-La Roche Inc.	Process for the preparation of aldehydes
US3978092A (en) *	1973-05-14	1976-08-31	Teijin Limited	Process for the preparation of unsaturated carbonyl compounds

1974
- 1974-08-09 GB GB35237/74A patent/GB1482614A/en not_active Expired
- 1974-08-09 AU AU72185/74A patent/AU7218574A/en not_active Expired
- 1974-08-14 IT IT26342/74A patent/IT1019970B/it active
- 1974-08-14 BE BE147594A patent/BE818839A/xx unknown
- 1974-08-14 DE DE2439140A patent/DE2439140C3/de not_active Expired
- 1974-08-15 BR BR6740/74A patent/BR7406740D0/pt unknown
- 1974-08-16 NL NL7410998A patent/NL7410998A/xx not_active Application Discontinuation
- 1974-08-16 CH CH1120774A patent/CH615144A5/de not_active IP Right Cessation
- 1974-08-19 FR FR7428450A patent/FR2254545B1/fr not_active Expired
1975
- 1975-04-25 FR FR7513068A patent/FR2274590A1/fr active Granted
1977
- 1977-11-30 US US05/856,179 patent/US4209644A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU7218574A (en)	1976-02-12
FR2254545B1 (da)	1982-01-29
BE818839A (fr)	1974-12-02
GB1482614A (en)	1977-08-10
DE2439140C3 (de)	1988-07-07
DE2439140A1 (de)	1975-03-20
FR2254545A1 (da)	1975-07-11
US4209644A (en)	1980-06-24
NL7410998A (nl)	1975-02-18
FR2274590A1 (fr)	1976-01-09
FR2274590B1 (da)	1978-10-13
BR7406740D0 (pt)	1975-05-27
DE2439140B2 (de)	1979-10-18
IT1019970B (it)	1977-11-30

Legal Events

Date	Code	Title	Description
1989-04-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
Schweizer et al.	1973	Reactions of phosphorus compounds. 33. Preparation of heterocyclic species from. alpha.-substituted vinyl phosphonium salts. Anomalous products from isopropenylphosphonium halides
DE2423409A1 (de)	1974-11-28	Verfahren zur herstellung von ungesaettigten carbonylverbindungen
DE2439140C3 (de)	1988-07-07	Allylacetalderivate
Inomata et al.	1978	New methods for the preparation of 3-substituted furans.
DE3013672A1 (de)	1981-10-15	2,4-dialkyl-2.6-heptadienal-derivate, verfahren zu deren herstellung und ihre anwendung als geruchs- und geschmacksstoffe
DE60320132T2 (de)	2009-05-20	Verfahren zur herstellung von diketenacetalen
DE3007592C2 (de)	1983-07-21	Verfahren zur Herstellung von substituierten Olefinen
DE2351376C3 (de)	1982-08-26	Verfahren zur Herstellung von 2-Brom-3-niederalkoxyacrolein
DE2462724C3 (de)	1982-01-28	Bicyclo-[2,2,2]-octanderivate und Verfahren zu deren Herstellung
DE2616528A1 (de)	1976-10-28	1,1,1-trihalogen-4-methylpentene sowie verfahren zu ihrer herstellung
DE2538532A1 (de)	1976-03-18	Verfahren zur herstellung stereospezifischer farnesylessigsaeure und deren ester
DE2754729A1 (de)	1978-06-15	Verfahren zur herstellung von vicinalen glykolen
DE19840746A1 (de)	2000-03-09	Verfahren zur Herstellung gamma,delta-ungesättigter Ketone durch Carroll-Reaktion
Newman et al.	1973	Novel synthesis of disubstituted maleic anhydrides by the pyrolysis of 1-ethoxy-1-alkenyl esters of. alpha.-keto acids
US2816117A (en)	1957-12-10	Chi ch
DE4027241A1 (de)	1991-03-07	Verfahren zur herstellung von (alpha)-alkyllactonen
Yadav et al.	1989	Synthesis of (IR)-(+)-cis-chrysanthemic acid
DE2934017C2 (da)	1987-07-23
Newkome et al.	1985	Chemistry of heterocyclic compounds series. 110. Synthesis of vinyl derivatives of phenanthroline and bipyridine
CH498809A (de)	1970-11-15	Verfahren zur Herstellung von Cyanhydrinen
JP4786267B2 (ja)	2011-10-05	ラクトンの製造方法及び製造されたラクトンの芳香物質としての用途
Yamashita et al.	1993	Syntheses of Naphthoquinone Compounds Using Chromium Carbonyl Carbene Complexes.
DE2551783C3 (de)	1980-08-14	Verfahren zur Isomerisierung eines der geometrischen Isomeren eines a , ß -ungesättigten Aldehydes in das entsprechende andere geometrische Isomere
Senda et al.	1992	The role of the nitrogen atom in the hydrogenation of piperidinones and methylenepiperidines
SU1735256A1 (ru)	1992-05-23	Способ получени замещенных монохлорциклопропанов