CH493565A - Verfahren zur Herstellung neuer quartärer Phosphoniumverbindungen - Google Patents

Verfahren zur Herstellung neuer quartärer Phosphoniumverbindungen

Info

Publication number: CH493565A
Authority: CH; Switzerland
Prior art keywords: group; formula; phosphonium; substituted; compound
Prior art date: 1966-05-19

Application number

CH686367A

Other languages

German (de)

English (en)

Inventor

Noordermeer Aart

Puister Willem

Johannes Wesselman Pe Gerardus

Original Assignee

Philips Nv

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.)

1966-05-19

Filing date

1967-05-16

Publication date

1970-07-15

1967-05-16 Application filed by Philips Nv filed Critical Philips Nv

1970-07-15 Publication of CH493565A publication Critical patent/CH493565A/de

Links

150000004023 quaternary phosphonium compounds Chemical class 0.000 title claims description 13
239000000543 intermediate Substances 0.000 title abstract description 5
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 42
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims abstract description 8
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims abstract description 8
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 8
235000019155 vitamin A Nutrition 0.000 claims abstract description 8
239000011719 vitamin A Substances 0.000 claims abstract description 8
229940045997 vitamin a Drugs 0.000 claims abstract description 8
150000004678 hydrides Chemical group 0.000 claims abstract description 5
125000005496 phosphonium group Chemical group 0.000 claims abstract description 5
125000002252 acyl group Chemical group 0.000 claims abstract description 4
-1 AlBr5 Chemical compound 0.000 claims description 17
229910015900 BF3 Inorganic materials 0.000 claims description 14
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 12
230000009467 reduction Effects 0.000 claims description 8
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910052987 metal hydride Inorganic materials 0.000 claims description 5
150000004681 metal hydrides Chemical class 0.000 claims description 5
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
150000004291 polyenes Polymers 0.000 claims description 3
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
150000001728 carbonyl compounds Chemical class 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
239000011592 zinc chloride Substances 0.000 claims description 2
235000005074 zinc chloride Nutrition 0.000 claims description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
125000001931 aliphatic group Chemical group 0.000 claims 1
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims 1
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 abstract description 7
150000001299 aldehydes Chemical class 0.000 abstract description 6
239000002253 acid Substances 0.000 abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 abstract description 4
125000003545 alkoxy group Chemical group 0.000 abstract description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
150000002148 esters Chemical class 0.000 abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract description 3
150000002576 ketones Chemical class 0.000 abstract description 3
238000001228 spectrum Methods 0.000 abstract description 2
229910000091 aluminium hydride Inorganic materials 0.000 abstract 1
235000021466 carotenoid Nutrition 0.000 abstract 1
150000001747 carotenoids Chemical class 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
238000003756 stirring Methods 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
239000000243 solution Substances 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 22
239000000203 mixture Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
238000004519 manufacturing process Methods 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 11
239000003208 petroleum Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
NCYCYZXNIZJOKI-OVSJKPMPSA-N Retinaldehyde Chemical compound O=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-OVSJKPMPSA-N 0.000 description 9
235000020945 retinal Nutrition 0.000 description 9
239000011604 retinal Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 8
238000002211 ultraviolet spectrum Methods 0.000 description 8
239000000370 acceptor Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 6
150000004714 phosphonium salts Chemical class 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000012456 homogeneous solution Substances 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 4
OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 4
235000013734 beta-carotene Nutrition 0.000 description 4
TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 4
239000011648 beta-carotene Substances 0.000 description 4
229960002747 betacarotene Drugs 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
229910010084 LiAlH4 Inorganic materials 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
230000008901 benefit Effects 0.000 description 3
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
UPYKUZBSLRQECL-UKMVMLAPSA-N Lycopene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1C(=C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=C)CCCC2(C)C UPYKUZBSLRQECL-UKMVMLAPSA-N 0.000 description 2
VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000001746 carotenes Chemical class 0.000 description 2
235000005473 carotenes Nutrition 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
239000000047 product Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
LDUGIPKKPRVPNI-UHFFFAOYSA-N (6-benzylidenecyclohexa-2,4-dien-1-yl)-diphenylphosphane Chemical compound C=1C=CC=CC=1C=C1C=CC=CC1P(C=1C=CC=CC=1)C1=CC=CC=C1 LDUGIPKKPRVPNI-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
101100004392 Arabidopsis thaliana BHLH147 gene Proteins 0.000 description 1
CNOPDZWOYFOHGN-BQYQJAHWSA-N Beta-Ionol Chemical compound CC(O)\C=C\C1=C(C)CCCC1(C)C CNOPDZWOYFOHGN-BQYQJAHWSA-N 0.000 description 1
VYGQUTWHTHXGQB-UHFFFAOYSA-N Retinol hexadecanoate Natural products CCCCCCCCCCCCCCCC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-UHFFFAOYSA-N 0.000 description 1
229910003074 TiCl4 Inorganic materials 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
CNOPDZWOYFOHGN-UHFFFAOYSA-N beta-ionol Natural products CC(O)C=CC1=C(C)CCCC1(C)C CNOPDZWOYFOHGN-UHFFFAOYSA-N 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003574 free electron Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005871 repellent Substances 0.000 description 1
229930002330 retinoic acid Natural products 0.000 description 1
229960000342 retinol acetate Drugs 0.000 description 1
235000019173 retinyl acetate Nutrition 0.000 description 1
239000011770 retinyl acetate Substances 0.000 description 1
QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 1
229940108325 retinyl palmitate Drugs 0.000 description 1
235000019172 retinyl palmitate Nutrition 0.000 description 1
239000011769 retinyl palmitate Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1

Classifications

- 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
- C07C403/24—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 six-membered non-aromatic rings, e.g. beta-carotene
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH686367A 1966-05-19 1967-05-16 Verfahren zur Herstellung neuer quartärer Phosphoniumverbindungen CH493565A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL6606914A NL6606914A (it)	1966-05-19	1966-05-19

Publications (1)

Publication Number	Publication Date
CH493565A true CH493565A (de)	1970-07-15

Family

ID=19796652

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH686367A CH493565A (de)	1966-05-19	1967-05-16	Verfahren zur Herstellung neuer quartärer Phosphoniumverbindungen

Country Status (8)

Country	Link
AT (1)	AT273163B (it)
BE (1)	BE698656A (it)
CH (1)	CH493565A (it)
DE (1)	DE1618741A1 (it)
ES (1)	ES340627A1 (it)
GB (1)	GB1180667A (it)
IT (1)	IT972009B (it)
NL (1)	NL6606914A (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3331008A1 (de) *	1983-08-27	1985-03-14	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von hydroxybenzylphosphoniumsalzen
NZ237758A (en) *	1990-04-17	1992-12-23	Shell Int Research	(phenylalkyl) triphenylphosphonium salt derivatives and fungicidal compositions

1966
- 1966-05-19 NL NL6606914A patent/NL6606914A/xx unknown
1967
- 1967-05-16 CH CH686367A patent/CH493565A/de not_active IP Right Cessation
- 1967-05-16 IT IT1615467A patent/IT972009B/it active
- 1967-05-16 GB GB2269367A patent/GB1180667A/en not_active Expired
- 1967-05-16 AT AT454767A patent/AT273163B/de active
- 1967-05-16 DE DE19671618741 patent/DE1618741A1/de active Pending
- 1967-05-17 ES ES340627A patent/ES340627A1/es not_active Expired
- 1967-05-18 BE BE698656D patent/BE698656A/xx unknown

Also Published As

Publication number	Publication date
AT273163B (de)	1969-08-11
GB1180667A (en)	1970-02-11
IT972009B (it)	1974-05-20
DE1618741A1 (de)	1971-03-11
BE698656A (it)	1967-11-20
ES340627A1 (es)	1968-06-01
NL6606914A (it)	1967-11-20

Legal Events

Date	Code	Title	Description
1981-01-30	PL	Patent ceased

Publication	Publication Date	Title
DE2760005C2 (de)	1984-04-26	Optisch aktive Norpinene und Verfahren zu ihrer Herstellung
DE2652256C2 (de)	1985-10-31	Polyprenylalkohole und diese enthaltende pharmazeutische Zusammensetzungen
DE68918241T2 (de)	1995-02-02	Phosphonatreagenz-Zusammensetzungen und Verfahren zu ihrer Herstellung.
DE2418715C2 (de)	1983-03-24	Allensäureester
EP0068350B1 (de)	1985-08-07	Verfahren zur Herstellung von Derivaten der Vinylphosphon- oder Vinylpyrophosphonsäure
DE2540283C3 (de)	1981-10-01	Verfahren zur Herstellung von carboxylgruppenhaltigen organischen Phosphorverbindungen
DE954247C (de)	1956-12-13	Verfahren zur Herstellung von ª‰-Carotin bzw. 15, 15'-Dehydro-ª‰-carotin
EP0090213A1 (de)	1983-10-05	Verfahren zur Herstellung von Derivaten der Vinylphosphon- oder Vinylpyrophosphonsäure
DE1618741A1 (de)	1971-03-11	Verfahren zur Herstellung neuer quartaerer Phosphoniumverbindungen
DE1816282A1 (de)	1969-07-17	Verfahren zur Herstellung von Hydroxy- oder Mercaptogruppen enthaltenden organischen Verbindungen
DE1125922B (de)	1962-03-22	Verfahren zur Herstellung von neuen Phosphoranverbindungen
EP0130439B1 (de)	1987-04-15	Verfahren zur Herstellung von Derivaten der Vinylphosphon-, oder Vinylpyrophosphonsäure
DE1167831B (de)	1964-04-16	Verfahren zur Herstellung von tertiaeren Diarylalkyl- oder Diaryl-aralkylphosphinoxydn
EP0144743B1 (de)	1988-01-07	Verfahren zur Herstellung organischer Chlorphosphane
DE2365322C3 (de)	1977-10-13	Subst.-Methyl-phosphonsäuredimethylester und ein Verfahren zu ihrer Herstellung
DE2355042A1 (de)	1974-05-22	Neue prostaglandinanaloge und verfahren zu deren herstellung
CH638780A5 (de)	1983-10-14	Cyclohexenderivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung der entsprechenden aldehyde.
DE2457555A1 (de)	1975-06-12	Verfahren zur herstellung von 1,2- disubstituierten trans-olefinen und zur herstellung von 2-alkenylphosphonsaeure- derivaten, die bei diesem verfahren als zwischenprodukte eingesetzt werden
DE1620705C3 (de)	1975-10-16	Verfahren zur Herstellung von substituierten 2-Alkoxy-carbonylmethyl-1,4,6,7-tetrahydro-11bH-benzo-(a)chinolizinen
AT239224B (de)	1965-03-25	Verfahren zur Herstellung von neuen, substituierten 2-Hydroxy-benzo[a]chinolizinen
DE1930334A1 (de)	1970-01-02	Substituierte Bis-(2-hydroxy-4-methyl-5-methylthiophenyl)methane und Verfahren zu deren Herstellung
AT221871B (de)	1962-06-25	Ungeziefervertilgungsmittel
DE2543732A1 (de)	1976-04-22	Derivate des 3alpha,5alpha-cyclo- 6beta-alkoxy-25-hydroxycholesterins und 3alpha,5alpha-cyclo-6beta-alkoxycholest- 22t-en-24,25-oxids, verfahren zur herstellung derselben und von zwischenprodukten fuer hydroxyliertes vitamin d tief 2 und d tief 3
DE3046059C2 (de)	1984-06-28	4-Halogen-5,5-dialkoxypentansäureester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von 2,2-Dialkyl-3-formylcyclopropancarbonsäureestern
DE2503313C3 (de)	1977-08-25	Verfahren zur Herstellung von transtrans-Muconsäure