GB619898A - A process for the manufacture of pentaenes - Google Patents
A process for the manufacture of pentaenesInfo
- 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
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.
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)
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 |
-
1946
- 1946-09-24 GB GB28500/46A patent/GB619898A/en not_active Expired
Cited By (2)
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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