GB619898A - A process for the manufacture of pentaenes - Google Patents

A process for the manufacture of pentaenes

Info

Publication number
GB619898A
GB619898A GB28500/46A GB2850046A GB619898A GB 619898 A GB619898 A GB 619898A GB 28500/46 A GB28500/46 A GB 28500/46A GB 2850046 A GB2850046 A GB 2850046A GB 619898 A GB619898 A GB 619898A
Authority
GB
United Kingdom
Prior art keywords
palladium
nonatriene
cyclohexene
dihydroxy
quinoline
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
GB28500/46A
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.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
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 Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB28500/46A priority Critical patent/GB619898A/en
Publication of GB619898A publication Critical patent/GB619898A/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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

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

Abstract

Pentaenes are manufactured by condensing b -ionone with a Grignard compound of 1-hydroxy-3-methyl-hexene-(2)-yne-(5) or an ether thereof, subjecting the condensation product to hydrogenation until 1 mol. of hydrogen has been added to the triple bond, rearranging, preferably in the presence of a diluent, the 1.7 - dihydroxy - 3.7 - dimethyl - 9 - (21.61.61 - tri - methyl-cyclohexene-(11)-yl)-nonatriene-(2.5.8) or an ether thereof, by the action of an acylating agent and splitting off acid. Hydrogenation may be effected catalytically, making use of palladium-calcium carbonate, palladium-barium sulphate or palladium-charcoal on to which quinoline has been adsorbed as catalysts. The rearrangement may be effected by heating with acetic anhydride in the presence of quinoline or by first esterifying 1.7 - dihydroxy - 3.7 - dimethyl-9-(21.6161-trimethyl-cyclohexene -(11)-yl)-nonatriene-2.5.8 and splitting off acid by boiling with tertiary potassium amylate. Detailed examples are given.
GB28500/46A 1946-09-24 1946-09-24 A process for the manufacture of pentaenes Expired GB619898A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB28500/46A GB619898A (en) 1946-09-24 1946-09-24 A process for the manufacture of pentaenes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB28500/46A GB619898A (en) 1946-09-24 1946-09-24 A process for the manufacture of pentaenes

Publications (1)

Publication Number Publication Date
GB619898A true GB619898A (en) 1949-03-16

Family

ID=10276620

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28500/46A Expired GB619898A (en) 1946-09-24 1946-09-24 A process for the manufacture of pentaenes

Country Status (1)

Country Link
GB (1) GB619898A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1005956B (en) * 1954-12-22 1957-04-11 Hoffmann La Roche Process for the production of vitamin A or its esters
US2924613A (en) * 1956-06-14 1960-02-09 Basf Ag Production of compounds of the vitamin-a series

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1005956B (en) * 1954-12-22 1957-04-11 Hoffmann La Roche Process for the production of vitamin A or its esters
US2924613A (en) * 1956-06-14 1960-02-09 Basf Ag Production of compounds of the vitamin-a series

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