GB631533A - Improvements in or relating to the manufacture of pentaenes - Google Patents

Improvements in or relating to the manufacture of pentaenes

Info

Publication number
GB631533A
GB631533A GB12271/47A GB1227147A GB631533A GB 631533 A GB631533 A GB 631533A GB 12271/47 A GB12271/47 A GB 12271/47A GB 1227147 A GB1227147 A GB 1227147A GB 631533 A GB631533 A GB 631533A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
methyl
hydrogenation
yne
trimethyl
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
GB12271/47A
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
Priority to GB12271/47A priority Critical patent/GB631533A/en
Publication of GB631533A publication Critical patent/GB631533A/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
    • C07C403/12—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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Vitamin A esters are obtained by condensing 4 - (21.61.61 - trimethyl - cyclohexene - (11) - yl)-2 - methyl - butene - (2) - al - (1) with a Grignard compound of 1 - hydroxy - 3 - methyl - pentane - (2) - yne - (4), subjecting the 1 - hydroxy-3.7 - dimethyl - 6 - hydroxy - 9 - (21.61.61-trimethyl - cyclohexane - (11) - yl) - nonadiene-(2.7) - yne - (4) formed to hydrogenation until 1 mol. of the hydrogen has been added to the triple bond of said hydroxy compound, treating the hydrogenation product with an esterifying agent to effect esterification of the terminal hydroxyl group and effecting dehydration and allyl rearrangement of the ester of 1-hydroxy-3.7 - dimethyl - 6 - hydroxy - 9 - (21.61.61-trimethyl-cyclohexene - (11) - yl) - nonatriene-(2.4.7) formed. In a modification the esterification may precede hydrogenation. Detailed examples are given in which hydrogenation precedes the esterification step. A sample has been furnished under Sect. 2(5) of Vitamin A acetate prepared by a process in which the hydrogenation is subsequent to esterification. 4 - (21.61.61 - trimethyl - cyclohexene - (11) - yl)-2 - methyl - butene - (2) - al - (1) is obtained from b -ionone by a glycide ester synthesis, saponification and decarboxylation of the glycide ester formed. 1 - Hydroxy - 3 - methyl - pentene - (2) - yne-(4) is obtained by reacting 3-hydroxy-3-methyl-pentene-(1)-yne-(4) the condensation product of methyl vinyl ketone and acetylene) with acids, rearrangement of the double bond and the hydroxyl group occurring thereby.
GB12271/47A 1947-05-06 1947-05-06 Improvements in or relating to the manufacture of pentaenes Expired GB631533A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB12271/47A GB631533A (en) 1947-05-06 1947-05-06 Improvements in or relating to the manufacture of pentaenes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB12271/47A GB631533A (en) 1947-05-06 1947-05-06 Improvements in or relating to the manufacture of pentaenes

Publications (1)

Publication Number Publication Date
GB631533A true GB631533A (en) 1949-11-04

Family

ID=10001487

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12271/47A Expired GB631533A (en) 1947-05-06 1947-05-06 Improvements in or relating to the manufacture of pentaenes

Country Status (1)

Country Link
GB (1) GB631533A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1028118B (en) * 1951-09-11 1958-04-17 Eastman Kodak Co Process for the production of vitamin A aldehyde, alcohol or its esters
US4825006A (en) * 1985-01-10 1989-04-25 Kuraray Co., Ltd. Process for producing vitamin A or its carboxylic acid esters, and intermediate compounds useful for the process

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1028118B (en) * 1951-09-11 1958-04-17 Eastman Kodak Co Process for the production of vitamin A aldehyde, alcohol or its esters
US4825006A (en) * 1985-01-10 1989-04-25 Kuraray Co., Ltd. Process for producing vitamin A or its carboxylic acid esters, and intermediate compounds useful for the process
US4876400A (en) * 1985-01-10 1989-10-24 Kuraray Co., Ltd. Process for producing vitamin A or its carboxylic acid esters, and itermediate compounds useful for the process

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