CH617168A5 - - Google Patents

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Publication number: CH617168A5
Authority: CH; Switzerland
Prior art keywords: formula; trimethyl; unsaturated; dimethyl; methyl
Prior art date: 1974-05-10

Application number

CH570175A

Other languages

German (de)

English (en)

Inventor

Michael Rosenberger

Gabriel Saucy

Original Assignee

Hoffmann La Roche

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.)

1974-05-10

Filing date

1975-05-02

Publication date

1980-05-14

1975-05-02 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1980-05-14 Publication of CH617168A5 publication Critical patent/CH617168A5/de

Links

RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
-1 aliphatic hydrocarbon radical Chemical group 0.000 description 44
238000000034 method Methods 0.000 description 33
150000001875 compounds Chemical class 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 15
150000002924 oxiranes Chemical class 0.000 description 13
150000001299 aldehydes Chemical class 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
238000009835 boiling Methods 0.000 description 10
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 10
229910001623 magnesium bromide Inorganic materials 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000004821 distillation Methods 0.000 description 9
239000002841 Lewis acid Substances 0.000 description 8
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
150000001340 alkali metals Chemical class 0.000 description 8
150000002576 ketones Chemical class 0.000 description 8
150000007517 lewis acids Chemical class 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000004215 Carbon black (E152) Substances 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000011777 magnesium Substances 0.000 description 6
229910052749 magnesium Inorganic materials 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000004593 Epoxy Substances 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
125000000392 cycloalkenyl group Chemical group 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
229910000272 alkali metal oxide Inorganic materials 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
235000021466 carotenoid Nutrition 0.000 description 3
150000001747 carotenoids Chemical class 0.000 description 3
239000003205 fragrance Substances 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
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 description 2
ISBNMTIKMIRSTI-UHFFFAOYSA-N 2,6,10-trimethylundeca-3,5,9-trienal Chemical compound O=CC(C)C=CC=C(C)CCC=C(C)C ISBNMTIKMIRSTI-UHFFFAOYSA-N 0.000 description 2
MOQGCGNUWBPGTQ-UHFFFAOYSA-N 2,6,6-trimethyl-1-cyclohexene-1-carboxaldehyde Chemical compound CC1=C(C=O)C(C)(C)CCC1 MOQGCGNUWBPGTQ-UHFFFAOYSA-N 0.000 description 2
NAXZOZQQIIMORY-UHFFFAOYSA-N 2,6,6-trimethylcyclohex-2-en-1-one Chemical compound CC1=CCCC(C)(C)C1=O NAXZOZQQIIMORY-UHFFFAOYSA-N 0.000 description 2
CVLUQCFBBAQDOH-UHFFFAOYSA-N 2-(2,6-dimethylhepta-1,5-dienyl)oxirane Chemical compound CC(C)=CCCC(C)=CC1CO1 CVLUQCFBBAQDOH-UHFFFAOYSA-N 0.000 description 2
HVDGAAPQCCUWDO-UHFFFAOYSA-N 2-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-enal Chemical compound O=CC(C)C=CC1=C(C)CCCC1(C)C HVDGAAPQCCUWDO-UHFFFAOYSA-N 0.000 description 2
AEMBVQYDXXTMIH-UHFFFAOYSA-N 4,8-dimethylnona-3,7-dienal Chemical compound CC(C)=CCCC(C)=CCC=O AEMBVQYDXXTMIH-UHFFFAOYSA-N 0.000 description 2
125000005330 8 membered heterocyclic group Chemical group 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
238000003476 Darzens condensation reaction Methods 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
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 description 2
ZVZRJSHOOULAGB-UHFFFAOYSA-N alpha-Cyclocitral Chemical compound CC1=CCCC(C)(C)C1C=O ZVZRJSHOOULAGB-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 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
GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000002035 hexane extract Substances 0.000 description 2
238000011905 homologation Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007858 starting material 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
VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 2
229940088594 vitamin Drugs 0.000 description 2
229930003231 vitamin Natural products 0.000 description 2
235000013343 vitamin Nutrition 0.000 description 2
239000011782 vitamin Substances 0.000 description 2
235000019155 vitamin A Nutrition 0.000 description 2
239000011719 vitamin A Substances 0.000 description 2
229940045997 vitamin a Drugs 0.000 description 2
HOXGZVUCAYFWGR-KQQUZDAGSA-N (3e,5e)-octa-1,3,5-triene Chemical compound CC\C=C\C=C\C=C HOXGZVUCAYFWGR-KQQUZDAGSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XEGOZCWNWANQIU-UHFFFAOYSA-N 2,6,10-trimethylundeca-2,5,9-trienal Chemical compound CC(C)=CCCC(C)=CCC=C(C)C=O XEGOZCWNWANQIU-UHFFFAOYSA-N 0.000 description 1
VFEUNYPJZDTDLX-UHFFFAOYSA-N 2,6-dimethylhepta-2,5-dienal Chemical compound CC(C)=CCC=C(C)C=O VFEUNYPJZDTDLX-UHFFFAOYSA-N 0.000 description 1
MWOSZASKCJRAKQ-UHFFFAOYSA-N 2,6-dimethylhepta-3,5-dienal Chemical compound O=CC(C)C=CC=C(C)C MWOSZASKCJRAKQ-UHFFFAOYSA-N 0.000 description 1
SZFVSTSEERLZST-UHFFFAOYSA-N 2,6-dimethylnona-2,6-diene Chemical compound CCC=C(C)CCC=C(C)C SZFVSTSEERLZST-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
UBTNVRPIHJRBCI-UHFFFAOYSA-N 6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trien-2-one Chemical compound CC(=O)C=CC=C(C)C=CC1=C(C)CCCC1(C)C UBTNVRPIHJRBCI-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
240000005265 Lupinus mutabilis Species 0.000 description 1
235000008755 Lupinus mutabilis Nutrition 0.000 description 1
235000019095 Sechium edule Nutrition 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940043350 citral Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
GZRYBYIBLHMWCD-UHFFFAOYSA-N dimethyl(methylidene)-$l^{4}-sulfane Chemical compound CS(C)=C GZRYBYIBLHMWCD-UHFFFAOYSA-N 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
KDFWIDQEGGGHAB-UHFFFAOYSA-N methylidene(diphenyl)-$l^{4}-sulfane Chemical compound C=1C=CC=CC=1S(=C)C1=CC=CC=C1 KDFWIDQEGGGHAB-UHFFFAOYSA-N 0.000 description 1
SOHCYNFHNYKSTM-UHFFFAOYSA-N methylsulfinylmethane;oxolane Chemical compound CS(C)=O.C1CCOC1 SOHCYNFHNYKSTM-UHFFFAOYSA-N 0.000 description 1
IRUCBBFNLDIMIK-UHFFFAOYSA-N oct-4-ene Chemical compound CCCC=CCCC IRUCBBFNLDIMIK-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical compound CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered 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
- C07C45/61—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
- 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
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
- 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)

CH570175A 1974-05-10 1975-05-02 CH617168A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/468,836 US4000131A (en)	1974-05-10	1974-05-10	Process for preparing epoxide-cyclohexyl compound and resultant compound

Publications (1)

Publication Number	Publication Date
CH617168A5 true CH617168A5 (fr)	1980-05-14

Family

ID=23861442

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH570175A CH617168A5 (fr)	1974-05-10	1975-05-02
CH104879A CH617687A5 (fr)	1974-05-10	1979-02-02

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH104879A CH617687A5 (fr)	1974-05-10	1979-02-02

Country Status (10)

Country	Link
US (1)	US4000131A (fr)
JP (1)	JPS50154203A (fr)
AT (2)	AT346850B (fr)
BE (1)	BE828865A (fr)
CH (2)	CH617168A5 (fr)
DE (1)	DE2520186A1 (fr)
FR (2)	FR2279707A1 (fr)
GB (1)	GB1478764A (fr)
IT (1)	IT1037500B (fr)
NL (1)	NL7505008A (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4211726A (en) *	1979-02-16	1980-07-08	American Cyanamid Company	Synthesis of substituted 9,10-anthracene-dicarboxaldehydes and 9,10-dihydro-9,10-anthracenedicarboxaldehydes
AU542623B2 (en) *	1980-05-16	1985-02-28	Bayer Aktiengesellschaft	1-hydroxyethyl-azole derivatives
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1974
- 1974-05-10 US US05/468,836 patent/US4000131A/en not_active Expired - Lifetime
1975
- 1975-04-21 IT IT22583/75A patent/IT1037500B/it active
- 1975-04-28 NL NL7505008A patent/NL7505008A/xx not_active Application Discontinuation
- 1975-05-02 CH CH570175A patent/CH617168A5/de not_active IP Right Cessation
- 1975-05-06 DE DE19752520186 patent/DE2520186A1/de not_active Withdrawn
- 1975-05-07 FR FR7514404A patent/FR2279707A1/fr active Granted
- 1975-05-08 JP JP50055333A patent/JPS50154203A/ja active Pending
- 1975-05-09 GB GB19625/75A patent/GB1478764A/en not_active Expired
- 1975-05-09 AT AT355475A patent/AT346850B/de not_active IP Right Cessation
- 1975-05-09 BE BE156171A patent/BE828865A/fr unknown
- 1975-10-09 FR FR7530908A patent/FR2275470A1/fr active Granted
1977
- 1977-08-05 AT AT0577877A patent/AT370714B/de not_active IP Right Cessation
1979
- 1979-02-02 CH CH104879A patent/CH617687A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS50154203A (fr)	1975-12-12
FR2279707A1 (fr)	1976-02-20
GB1478764A (en)	1977-07-06
FR2275470A1 (fr)	1976-01-16
IT1037500B (it)	1979-11-10
ATA577877A (de)	1982-09-15
BE828865A (fr)	1975-11-10
FR2275470B1 (fr)	1980-05-30
AT370714B (de)	1983-04-25
DE2520186A1 (de)	1975-11-27
AT346850B (de)	1978-11-27
US4000131A (en)	1976-12-28
NL7505008A (nl)	1975-11-12
CH617687A5 (fr)	1980-06-13
ATA355475A (de)	1978-04-15
FR2279707B1 (fr)	1978-07-13

Legal Events

Date	Code	Title	Description
1982-01-29	PL	Patent ceased

Publication	Publication Date	Title
CH617168A5 (fr)	1980-05-14
EP0633258A1 (fr)	1995-01-11	Procédé amélioré de production d'astaxantin, nouveaux produits intermédiares et procédé de leur préparation
EP0004621B1 (fr)	1984-05-09	Procédé de préparation en plusieurs étapes de la zéaxanthine et de l'alloxanthine à partir de dérivés de la cyclohexanone ou du cyclohexanol; dérivés de la cyclohexanone et du cyclohexanol
DE2801908A1 (de)	1978-07-20	Cyclohexenderivate
EP0037584A1 (fr)	1981-10-14	2.4-Dialcoyl-2.6-heptadiénals et -heptadiénols, procédé pour leur préparation et leur utilisation à titre d'ingrédients parfumants et aromatisants
EP0107806B1 (fr)	1989-05-24	Procédé pour la préparation de dérivés optiquement actifs d'hydroquinone et du tocophérol
EP0644186A1 (fr)	1995-03-22	Procédé pour la préparation d'acide 13-(Z)-retinoique.
EP0001089B1 (fr)	1981-10-21	Procédé de préparation de 2-tetrahydrofurannones substituées par un radical halogénovinyle; certaines 2-tetrahydrofurannones substituées par un radical halogénovinyle
EP0116277A2 (fr)	1984-08-22	Cétones de composés bicycliques, procédé pour leur préparation, compositions odoriférantes et/ou aromatisantes contenant ces composés
EP1241157A1 (fr)	2002-09-18	Procédé pour la préparation de 2,7-diméthyl-2,4,6-octatriénal-monoacétals
DE2225612C2 (de)	1982-07-01	Cyclische Methyl-fumardialdehyd-monoacetale und Verfahren zu ihrer Herstellung
EP0031875B1 (fr)	1983-05-18	Procédé pour la préparation de dérivés de cyclohexène
EP0194591B1 (fr)	1988-08-24	Procédé de préparation de 2-alkyl-cyclopentanones
DE2432232C2 (de)	1982-09-16	Verfahren zur Herstellung &gamma;,&delta;-ungesättigter Ketone
DE1793711C3 (de)	1980-01-31	Verfahren zur Herstellung eines ungesättigten Aldehyds
EP0882709A1 (fr)	1998-12-09	Procédé pour la préparation de la zéaxanthine, intermédiaires pour ce procédé et procédé pour leur préparation
EP0415190B1 (fr)	1994-01-19	Dérivés de cycloalkylidène
DE2824841C3 (de)	1981-04-02	Verfahren zur Herstellung von 2-Cyclopentenonderivaten sowie diese enthaltende Parfüm-Kompositionen
EP0001553B1 (fr)	1980-10-29	Composés bicycliques odoriférants, procédé de leur préparation et leur précurseur
DE2630755A1 (de)	1977-01-20	Verfahren zur herstellung von polyenen
DE2166797C2 (de)	1985-08-29	Optisch aktive tricyclische Lactonaldehyde und Verfahren zu deren Herstellung
DE1768659C3 (de)	1977-07-28	Verfahren zur Herstellung von ß-Sinensal
EP0671378B1 (fr)	1997-01-29	Procédé de préparation de la (1R,4S)-4-hydroxy-1,2,2-triméthylcyclopentyl-méthylcétone, de ses dérivés et stéréoisomères
EP0040353B1 (fr)	1983-12-14	Procédé de préparation de linéatine
DE3027689A1 (de)	1982-02-18	Verfahren zur herstellung von (alpha) - und (beta) -cyclocitral sowie die n-methylaldimine dieser verbindungen