DD209460A5 - Verfahren zur herstellung von 2-exo-oxy-7-oxabicyclo(2,2,1)heptan - Google Patents

Verfahren zur herstellung von 2-exo-oxy-7-oxabicyclo(2,2,1)heptan Download PDF

Info

Publication number: DD209460A5
Authority: DD; German Democratic Republic
Prior art keywords: group; alkyl; atoms; hydrogen atom; optionally substituted
Prior art date: 1981-12-16

Application number

DD82245938A

Other languages

German (de)

English (en)

Inventor

Payne

Original Assignee

Shell Int Research

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.)

1981-12-16

Filing date

1982-12-14

Publication date

1984-05-09

1982-12-14 Application filed by Shell Int Research filed Critical Shell Int Research

1984-05-09 Publication of DD209460A5 publication Critical patent/DD209460A5/de

Links

IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title claims abstract description 25
238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 29
239000002253 acid Substances 0.000 claims abstract description 20
238000002360 preparation method Methods 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
150000001875 compounds Chemical class 0.000 claims description 32
-1 hydroxycarbonyl group Chemical group 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 16
229910052801 chlorine Inorganic materials 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 13
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
125000001246 bromo group Chemical group Br* 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
239000003054 catalyst Substances 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
150000002170 ethers Chemical class 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
239000007800 oxidant agent Substances 0.000 claims description 7
QHDHNVFIKWGRJR-UHFFFAOYSA-N 1-cyclohexenol Chemical compound OC1=CCCCC1 QHDHNVFIKWGRJR-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
PQANGXXSEABURG-UHFFFAOYSA-N cyclohexenol Natural products OC1CCCC=C1 PQANGXXSEABURG-UHFFFAOYSA-N 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
238000006735 epoxidation reaction Methods 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
FYTJMUYAPJUVHO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-6-ol Chemical compound C1CCCC2OC21O FYTJMUYAPJUVHO-UHFFFAOYSA-N 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
239000011203 carbon fibre reinforced carbon Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000011541 reaction mixture Substances 0.000 claims description 2
238000011084 recovery Methods 0.000 claims description 2
229910052723 transition metal Inorganic materials 0.000 claims description 2
150000003624 transition metals Chemical class 0.000 claims description 2
OULAQVCZRNCPNC-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ol Chemical compound C1C(O)CCC2OC21 OULAQVCZRNCPNC-UHFFFAOYSA-N 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 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
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
239000004593 Epoxy Substances 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
125000003700 epoxy group Chemical group 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
239000000047 product Substances 0.000 description 26
239000000243 solution Substances 0.000 description 26
239000000203 mixture Substances 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
238000009835 boiling Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
238000004821 distillation Methods 0.000 description 14
239000003921 oil Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
235000019198 oils Nutrition 0.000 description 8
238000010992 reflux Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000010410 layer Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
POKCGQXKNIJLCR-UHFFFAOYSA-N 4-methylcyclohex-3-en-1-one Chemical compound CC1=CCC(=O)CC1 POKCGQXKNIJLCR-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000002924 oxiranes Chemical group 0.000 description 4
229910052720 vanadium Inorganic materials 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001335 aliphatic alkanes Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
ABZZOPIABWYXSN-UHFFFAOYSA-N cyclohex-3-en-1-ol Chemical class OC1CCC=CC1 ABZZOPIABWYXSN-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
150000003413 spiro compounds Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
HDNRAPAFJLXKBV-UHFFFAOYSA-N 1-ethyl-4-methoxybenzene Chemical compound CCC1=CC=C(OC)C=C1 HDNRAPAFJLXKBV-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
YCTDZYMMFQCTEO-UHFFFAOYSA-N 3-octene Chemical compound CCCCC=CCC YCTDZYMMFQCTEO-UHFFFAOYSA-N 0.000 description 2
XWWZJGOBESJRBC-UHFFFAOYSA-N 4,6,6-trimethyl-3-[4,6,6-trimethyl-3-(4,6,6-trimethyl-3-bicyclo[3.1.1]hept-4-enyl)-3-bicyclo[3.1.1]hept-4-enyl]bicyclo[3.1.1]hept-4-en-2-ol Chemical compound OC1C(C2)C(C)(C)C2=C(C)C1C1(C(=C2CC(C2(C)C)C1)C)C1CC(C2(C)C)CC2=C1C XWWZJGOBESJRBC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
RTLTXXDTPFWZLO-UHFFFAOYSA-N Terpinolene oxide Chemical compound C1CC(C)=CCC21C(C)(C)O2 RTLTXXDTPFWZLO-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
150000004965 peroxy acids Chemical class 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
WRYLYDPHFGVWKC-JTQLQIEISA-N (R)-(-)-p-Menth-1-en-4-ol Natural products CC(C)[C@@]1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-JTQLQIEISA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 1
WRSPKOHCDLYMIR-UHFFFAOYSA-N 1-oxaspiro[2.5]oct-5-ene Chemical compound C1OC11CC=CCC1 WRSPKOHCDLYMIR-UHFFFAOYSA-N 0.000 description 1
RPABADYMEMUBEC-UHFFFAOYSA-N 1-oxaspiro[4.5]decan-8-one Chemical compound C1CC(=O)CCC11OCCC1 RPABADYMEMUBEC-UHFFFAOYSA-N 0.000 description 1
BNMCDVQCTYJLBZ-UHFFFAOYSA-N 2,2,4,6,6-pentamethylcyclohex-3-en-1-one Chemical compound CC1=CC(C)(C)C(=O)C(C)(C)C1 BNMCDVQCTYJLBZ-UHFFFAOYSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
WRYLYDPHFGVWKC-SNVBAGLBSA-N 4-Terpineol Natural products CC(C)[C@]1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-SNVBAGLBSA-N 0.000 description 1
JEFSGXDPIHRGAV-UHFFFAOYSA-N 5-methoxy-2-methylcyclohexa-1,3-diene Chemical compound COC1CC=C(C)C=C1 JEFSGXDPIHRGAV-UHFFFAOYSA-N 0.000 description 1
238000006027 Birch reduction reaction Methods 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000004849 alkoxymethyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
ADKBGLXGTKOWIU-UHFFFAOYSA-N butanediperoxoic acid Chemical compound OOC(=O)CCC(=O)OO ADKBGLXGTKOWIU-UHFFFAOYSA-N 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000004927 fusion Effects 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
150000008301 phosphite esters Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
150000005199 trimethylbenzenes Chemical class 0.000 description 1
JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
PSDQQCXQSWHCRN-UHFFFAOYSA-N vanadium(4+) Chemical compound [V+4] PSDQQCXQSWHCRN-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
- C07C35/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings with unsaturation at least in the ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/48—Halogenated derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1781—Unsaturated ethers containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
- 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
- C07C45/513—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 etherified hydroxyl group
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- 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)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Epoxy Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD82245938A 1981-12-16 1982-12-14 Verfahren zur herstellung von 2-exo-oxy-7-oxabicyclo(2,2,1)heptan DD209460A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US33109581A	1981-12-16	1981-12-16

Publications (1)

Publication Number	Publication Date
DD209460A5 true DD209460A5 (de)	1984-05-09

Family

ID=23292603

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82245938A DD209460A5 (de)	1981-12-16	1982-12-14	Verfahren zur herstellung von 2-exo-oxy-7-oxabicyclo(2,2,1)heptan

Country Status (18)

Country	Link
EP (1)	EP0081892B1 (cs)
JP (1)	JPS58110590A (cs)
KR (1)	KR880001427B1 (cs)
AT (1)	ATE25982T1 (cs)
AU (1)	AU556104B2 (cs)
BG (1)	BG38637A3 (cs)
BR (1)	BR8207274A (cs)
CA (1)	CA1255320A (cs)
CS (1)	CS248036B2 (cs)
DD (1)	DD209460A5 (cs)
DE (1)	DE3275721D1 (cs)
DK (1)	DK525982A (cs)
ES (1)	ES8405404A1 (cs)
HU (1)	HU190431B (cs)
IE (1)	IE53986B1 (cs)
IL (1)	IL67473A (cs)
PL (1)	PL139922B1 (cs)
ZA (1)	ZA829185B (cs)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4579582A (en) *	1982-08-18	1986-04-01	Chevron Research Company	5-deoxy-3-O-arylmethyl or substituted arylmethyl-1,2-O-alkylidene-α-D-xylofuranose herbicide derivatives
GB8321713D0 (en) *	1983-08-12	1983-09-14	Shell Int Research	Preparing oxabicycloalkane compounds
US4606753A (en) *	1984-06-15	1986-08-19	Shell Oil Company	4-substituted-2-oxabicyclo[2.2.1]heptane ether herbicides
US4883888A (en) *	1984-07-13	1989-11-28	The Procter & Gamble Company	Oxa-fenchyl amines useful for preparing high intensity sweeteners
FR2996551B1 (fr) *	2012-10-05	2015-01-09	Mane Fils V	Procede de synthese de cyclohexenones ainsi que leur utilisation en parfumerie
WO2016061193A1 (en) *	2014-10-15	2016-04-21	Lixte Biotechnology, Inc.	Process of synthesizing 3-(4-methylpiperazine-1-carbonyl)-7-oxabicyclo[2.2.1] heptane-2-carboxylic acid
WO2018210663A1 (en) *	2017-05-19	2018-11-22	BASF Agro B.V.	A method for separating optically active hydroxy cineole derivatives
JP2025503957A (ja)	2022-01-26	2025-02-06	ビーエーエスエフソシエタス・ヨーロピア	４－イソプロピル－１－メチル－７－オキサビシクロ［２．２．１］ヘプタン－２－オール又はそのエステル若しくはエーテルを含む組成物、及び芳香化学物質としてのそれらの使用
EP4627025A1 (en)	2022-12-02	2025-10-08	Basf Se	Esters and ethers of 5-isopropyl-2-methylcyclohexan-1-ol as fragrance ingredients

1982
- 1982-11-25 DK DK525982A patent/DK525982A/da not_active Application Discontinuation
- 1982-12-01 CA CA000416781A patent/CA1255320A/en not_active Expired
- 1982-12-11 AU AU91488/82A patent/AU556104B2/en not_active Ceased
- 1982-12-14 JP JP57217923A patent/JPS58110590A/ja active Granted
- 1982-12-14 DD DD82245938A patent/DD209460A5/de not_active IP Right Cessation
- 1982-12-14 IE IE2968/82A patent/IE53986B1/en unknown
- 1982-12-14 BG BG058910A patent/BG38637A3/xx unknown
- 1982-12-14 CS CS829132A patent/CS248036B2/cs unknown
- 1982-12-14 KR KR8205589A patent/KR880001427B1/ko not_active Expired
- 1982-12-14 PL PL1982239510A patent/PL139922B1/pl unknown
- 1982-12-14 IL IL67473A patent/IL67473A/xx unknown
- 1982-12-14 HU HU824030A patent/HU190431B/hu not_active IP Right Cessation
- 1982-12-14 ES ES518158A patent/ES8405404A1/es not_active Expired
- 1982-12-14 ZA ZA829185A patent/ZA829185B/xx unknown
- 1982-12-14 BR BR8207274A patent/BR8207274A/pt not_active IP Right Cessation
- 1982-12-15 EP EP82201608A patent/EP0081892B1/en not_active Expired
- 1982-12-15 DE DE8282201608T patent/DE3275721D1/de not_active Expired
- 1982-12-15 AT AT82201608T patent/ATE25982T1/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS58110590A (ja)	1983-07-01
IE53986B1 (en)	1989-05-10
KR840002822A (ko)	1984-07-21
JPH0365348B2 (cs)	1991-10-11
CA1255320A (en)	1989-06-06
HU190431B (en)	1986-09-29
BR8207274A (pt)	1983-10-18
ATE25982T1 (de)	1987-04-15
PL239510A1 (en)	1984-01-16
BG38637A3 (en)	1986-01-15
IE822968L (en)	1983-06-16
DK525982A (da)	1983-06-17
EP0081892A2 (en)	1983-06-22
DE3275721D1 (en)	1987-04-23
AU9148882A (en)	1983-06-23
CS248036B2 (en)	1987-01-15
EP0081892A3 (en)	1984-05-02
EP0081892B1 (en)	1987-03-18
IL67473A (en)	1986-11-30
AU556104B2 (en)	1986-10-23
KR880001427B1 (ko)	1988-08-08
ES518158A0 (es)	1984-06-01
ZA829185B (en)	1983-09-28
ES8405404A1 (es)	1984-06-01
IL67473A0 (en)	1983-05-15
PL139922B1 (en)	1987-03-31

Legal Events

Date	Code	Title	Description
1995-12-07	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
US4487945A (en)	1984-12-11	Preparation of 2-exo-Hydroxy-7-oxabicyclo[2.2.1]heptanes
DE2760005C2 (de)	1984-04-26	Optisch aktive Norpinene und Verfahren zu ihrer Herstellung
DD209460A5 (de)	1984-05-09	Verfahren zur herstellung von 2-exo-oxy-7-oxabicyclo(2,2,1)heptan
DE69213916T2 (de)	1997-03-06	Verfahren zur Herstellung von L-Ambrox
EP0107857A1 (de)	1984-05-09	Verfahren zur Herstellung von 8.12-Epoxy-13.14.15.16-tetranorlabdan
DE3712464A1 (de)	1987-10-15	Neue halogenierte heterocyclische aetherverbindungen, ihre herstellung, diese verbindungen enthaltende herbicide und ihre anwendung zur regulierung des pflanzenwachstums
DE2511410C2 (de)	1983-10-20	12-Oxo-15-hydroxy-tetradecancarbonsäurelactone und Verfahren zu ihrer Herstellung
DE3050772C2 (cs)	1989-03-09
DE2065322C3 (de)	1980-03-20	Cycloaliphatisch ungesättigte Epoxyverbindungen und Verfahren zu ihrer Herstellung
EP0236884B1 (de)	1990-12-27	Verfahren zur Herstellung von Phenoxyalkanoltriazolverbindungen und Zwischenprodukte hierfür
DE2718057A1 (de)	1977-11-17	Verfahren zur herstellung von epoxiden
DE69718282T2 (de)	2003-11-27	Neue Epoxiden, Verfahren zu ihrer Herstellung und ihre Verwendung für die Herstellung von Riechstoff-Bestandteilen
DE1618782A1 (de)	1971-01-28	Neue tricyclische Verbindungen und Verfahren zur Herstellung von tricyclischen Verbindungen
DE3233175A1 (de)	1983-03-17	Verfahren zur herstellung von (delta)- und (epsilon)-damascon
DE60315391T2 (de)	2008-04-17	Optisch aktive Epoxyverbindungen und Verfahren zu deren Herstellung
DE1019307B (de)	1957-11-14	Verfahren zur Herstellung von Epoxyverbindungen
DE2856721A1 (de)	1979-07-12	Verfahren zur herstellung von cyclohex-3-en-1-onen
EP0558952B1 (de)	1996-12-27	Fluorsubstituierte Epoxycyclo- und Epoxybicyclo(2.2.1)Heptan-Derivate sowie Verfahren zur Herstellung
DE1593387C (de)	1971-09-09	Verfahren zur Herstellung eines Di hydrochrysanthemolactons
DE2534859C2 (de)	1982-12-30	Verfahren zur Herstellung von 2(E)-,4(Z)- ungesättigten Estern
DE69706786T2 (de)	2002-05-23	Herstellung von Norlabdan-Oxid-Zwischenprodukten
DE1079635B (de)	1960-04-14	Verfahren zur Herstellung halogenhaltiger organischer Peroxyde
DE2166795C2 (de)	1985-04-11	Verfahren zur Trennung racemischer Gemische von Oxo-Verbindungen
DE2734085A1 (de)	1979-02-22	Verfahren zur herstellung von halogenalkylsubstituierten oxiranen
EP0000555B1 (de)	1982-02-10	Verfahren zur Herstellung von halogenalkylsubstituierten Oxiranen