GB1443992A - Process for the manufacture of polyene compounds - Google Patents

Process for the manufacture of polyene compounds

Info

Publication number
GB1443992A
GB1443992A GB5098873A GB5098873A GB1443992A GB 1443992 A GB1443992 A GB 1443992A GB 5098873 A GB5098873 A GB 5098873A GB 5098873 A GB5098873 A GB 5098873A GB 1443992 A GB1443992 A GB 1443992A
Authority
GB
United Kingdom
Prior art keywords
formula
compounds
alkyl
nov
manufacture
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB5098873A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1443992A publication Critical patent/GB1443992A/en
Expired legal-status Critical Current

Links

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
    • C07C403/06—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 singly-bound oxygen atoms
    • C07C403/08—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 singly-bound oxygen atoms by hydroxy groups
    • 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
    • C07C403/06—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 singly-bound oxygen atoms
    • C07C403/10—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 singly-bound oxygen atoms by etherified hydroxy groups
    • 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
    • C07C403/06—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 singly-bound oxygen atoms
    • C07C403/12—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 singly-bound oxygen atoms by esterified hydroxy groups
    • 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
    • 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
    • C07C403/20—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 carboxyl groups or halides, anhydrides, or (thio)esters thereof
    • 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
    • C07B2200/09—Geometrical 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

Abstract

1443992 Polyene compounds F HOFFMANN-LA ROCHE & CO AG 2 Nov 1973 [2 Nov 1972] 50988/73 Heading C2C The invention comprises compounds of the formula where R 20 is CH 2 OR 1 or-COOR 1 where R 1 is alxanoyl of 2-18 carbon atoms or aroyl and R 1 is alkyl, aryl or aralkyl. The compounds may be prepared by heating a compound of the formula in an inert organic solvent in the presence of a siloxy vanadium oxide catalyst of the formula where R 4 is C 1 -C 6 alkyl, cycloalkyl, C 1 -C 6 alkyl substituted cycloalxyl, phenyl, C 1 -C 6 alkyl substituted phenyl or aralxyl, R 5 has any of the values accorded to R 4 or is (R 4 ) 3 Si-, m is 1-3 and n 0-2, with the proviso that the sum of m and n is 3. The all-trans isomers of the compounds of Formula I are obtained by treating other isomers with an organic amine base or an organic acid.
GB5098873A 1972-11-02 1973-11-02 Process for the manufacture of polyene compounds Expired GB1443992A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US30316272A 1972-11-02 1972-11-02

Publications (1)

Publication Number Publication Date
GB1443992A true GB1443992A (en) 1976-07-28

Family

ID=23170788

Family Applications (3)

Application Number Title Priority Date Filing Date
GB5098873A Expired GB1443992A (en) 1972-11-02 1973-11-02 Process for the manufacture of polyene compounds
GB1897475A Expired GB1443993A (en) 1972-11-02 1973-11-02 Polyene compounds
GB1897575A Expired GB1443994A (en) 1972-11-02 1973-11-02 Process for the manufactu5e of polyene compounds

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB1897475A Expired GB1443993A (en) 1972-11-02 1973-11-02 Polyene compounds
GB1897575A Expired GB1443994A (en) 1972-11-02 1973-11-02 Process for the manufactu5e of polyene compounds

Country Status (5)

Country Link
JP (1) JPS4976838A (en)
CH (1) CH601217A5 (en)
DE (1) DE2354792A1 (en)
FR (1) FR2212329B1 (en)
GB (3) GB1443992A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5086060A (en) * 1989-07-25 1992-02-04 Eastman Kodak Company Compound and method for treating skin for acne or psoriasis
US20230125156A1 (en) * 2020-03-31 2023-04-27 Dsm Ip Assets B.V. Process for production of vitamin a

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL74807C (en) *
US2451735A (en) * 1945-10-18 1948-10-19 Hoffmann La Roche Polyenes and process for the manufacture thereof
US2451738A (en) * 1945-10-18 1948-10-19 Hoffmann La Roche Process for the manufacture of pentaenes
US2451739A (en) * 1945-10-18 1948-10-19 Hoffmann La Roche Process for the manufacture of pentaenes
US2451736A (en) * 1945-10-18 1948-10-19 Hoffmann La Roche Polyenes and process for the manufacture thereof
DE833960C (en) * 1949-12-19 1952-03-13 Glaxo Lab Ltd Process for the preparation of 3, 7-dimethyl-1- (1-oxy-2, 6, 6-trimethylcyclohex-1-yl) -nona-3, 5, 7-trien-1-yn-9-ol

Also Published As

Publication number Publication date
DE2354792A1 (en) 1974-05-09
JPS4976838A (en) 1974-07-24
FR2212329A1 (en) 1974-07-26
FR2212329B1 (en) 1977-09-23
GB1443993A (en) 1976-07-28
CH601217A5 (en) 1978-06-30
GB1443994A (en) 1976-07-28

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee