GB653679A - Improvements in or relating to the production of compounds having vitamin a activity - Google Patents

Improvements in or relating to the production of compounds having vitamin a activity

Info

Publication number
GB653679A
GB653679A GB1706/48A GB170648A GB653679A GB 653679 A GB653679 A GB 653679A GB 1706/48 A GB1706/48 A GB 1706/48A GB 170648 A GB170648 A GB 170648A GB 653679 A GB653679 A GB 653679A
Authority
GB
United Kingdom
Prior art keywords
benzene
acid
hydrogenation
dehydration
effected
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
GB1706/48A
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.)
Ortho Pharmaceutical Corp
Original Assignee
Ortho Pharmaceutical Corp
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 Ortho Pharmaceutical Corp filed Critical Ortho Pharmaceutical Corp
Publication of GB653679A publication Critical patent/GB653679A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00Derivatives 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
    • C07C403/06Derivatives 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
    • C07C403/10Derivatives 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compounds having vitamin A activity are obtained by subjecting a compound of the formula <FORM:0653679/IV (b)/1> to hydrogenation to produce a compound of the formula <FORM:0653679/IV (b)/2> which is subjected to alkali isomerization and if desired dehydrated. Preferably the hydrogenation is effected catalytically using a poisoned Raney nickel catalyst and the alkali isomerization is effected by treating the hydrogenated compound with a strongly alkaline substance such as sodium hydroxide, a sodium alkoxide in alcohol, or a quaternary ammonium hydroxide. Dehydration may be effected using benzoyl chloride in pyridine, acetyl chloride in dimethyl aniline, glacial acetic acid, glacial acetic acid and potassium acetate, toluenesulphonic acid in benzene, oxalic acid in benzene, glacial acetic acid in benzene, catalytic quantities of iodine in benzene and phenyl isocyanate in benzene. Detailed examples are given. The Specification as open to inspection under Sect. 91 comprises the steps of hydrogenation, dehydration, and acid or alkali isomerization in any desired order but excludes these steps in the order of hydrogenation, acid isomerization and dehydration. This subject-matter does not appear in the Specification as accepted.
GB1706/48A 1947-10-03 1948-01-20 Improvements in or relating to the production of compounds having vitamin a activity Expired GB653679A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US653679XA 1947-10-03 1947-10-03

Publications (1)

Publication Number Publication Date
GB653679A true GB653679A (en) 1951-05-23

Family

ID=22062222

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1706/48A Expired GB653679A (en) 1947-10-03 1948-01-20 Improvements in or relating to the production of compounds having vitamin a activity

Country Status (1)

Country Link
GB (1) GB653679A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1027661B (en) * 1954-04-22 1958-04-10 Eastman Kodak Co Process for the production of vitamin A-aldehyde from 3, 7-dioxyvitamin A-aldehyde acetals

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1027661B (en) * 1954-04-22 1958-04-10 Eastman Kodak Co Process for the production of vitamin A-aldehyde from 3, 7-dioxyvitamin A-aldehyde acetals

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