GB786104A - Preparation of unsaturated polyene compounds - Google Patents
Preparation of unsaturated polyene compoundsInfo
- Publication number
- GB786104A GB786104A GB18885/55A GB1888555A GB786104A GB 786104 A GB786104 A GB 786104A GB 18885/55 A GB18885/55 A GB 18885/55A GB 1888555 A GB1888555 A GB 1888555A GB 786104 A GB786104 A GB 786104A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimethyl
- hydroxy
- cyclohexen
- carboxy
- anhydride
- 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
- C07C403/02—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 containing only carbon and hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises a compound having the formula <FORM:0786104/IV (a)/1> and a process for preparing an unsaturated polyene compound comprising contacting a b -hydroxy carboxylic acid of the formula <FORM:0786104/IV (a)/2> wherein R is a conjugated polyene radical, each of the symbols R1 and R11 is a hydrogen atom or a lower alkyl radical, and R111 is a hydrogen atom, a lower alkyl radical or a conjugated polyene radical, with an acid anhydride under substantially anhydrous conditions to form a compound having the formula <FORM:0786104/IV (a)/3> As acid anhydrides there may beused acetic anhydride, n-butyric anhydride, n-propionic anhydride, n-caproic anhydride, phthalic anhydride and succinic anhydride. Starting materials, some of which are used in the examples, are 1-(2,6,6-trimethyl-1-cyclohexen-1-yl) - 3,7 - dimethyl - 7 - hydroxy - 8 - carboxyl-1,3,5-nonatriene and the corresponding octatriene, 1 - (2,6,6 - trimethyl - 1 - cyclohexen - 1 - yl) - 3 - methyl - 3 - hydroxy - 4 - carboxy - 1 - pentene and the corresponding butene, 1-(2,6,6-trimethyl - 1 - cyclohexen - 1 - yl) - 3,7,10 - trimethyl - 9 - hydroxy - 10 - carboxy - 1,3,5,7-decatetraene, 1 - (2,6,6 - trimethyl - 1 - cyclohexen - 1 - yl) - 3,7 - dimethyl - 9 - hydroxy - 10 - carboxy - 1,3,5,7,11 - dodecapentaene, 1 - (2,6,6-trimethyl - 1 - cyclohexen - 1 - yl) - 3,7,11 - trimethyl - 9 - hydroxy - 10 - carboxy - 1,3,5,7,11 - dodecapentaene, 1 - (2,6,6 - trimethyl - 1 - cyclohexen - 1 - yl) - 3,7 - dimethyl - 9 - butyl - 9 - hydroxy - 10 - carboxy - 1,3,5,7 - decatetraene, 1 - (2,6,6 - trimethyl - 1 - cyclohexen - 1 - yl) - 3,7,10 - trimethyl - 9 - hydroxy - 10 - carboxy - 1,3,5,7 - dodecatetraene, 1 - (2,6,6 - trimethyl-1-cyclohexen - 1 - yl) - 3,7,10 - trimethyl - 9 - hydroxy - 10 - carboxy - 1,3,5,7 - tridecatetraene, and 6 - hydroxy - 7 - carboxy - 2,4 - heptadiene. Starting compound. 1 - (2,6,6 - Trimethyl - 1-cyclohexen - 1 - yl) - 3,7,10 - trimethyl-9-hydroxy-10 - carboxy - 1,3,5,7 - decatetraene is obtained by condensing Vitamin A aldehyde with a -bromo-propionate in the presence of zinc and hydrolysing the b -hydroxy ester thus produced.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US786104XA | 1954-07-01 | 1954-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB786104A true GB786104A (en) | 1957-11-13 |
Family
ID=22145143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18885/55A Expired GB786104A (en) | 1954-07-01 | 1955-06-30 | Preparation of unsaturated polyene compounds |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH336063A (en) |
| DE (1) | DE1001258C2 (en) |
| FR (1) | FR1211308A (en) |
| GB (1) | GB786104A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4523042A (en) * | 1983-07-29 | 1985-06-11 | Usv Pharmaceutical | Derivatives of alpha-alkyl polyolefinic carboxylic acid useful in the treatment of psoriasis |
-
1955
- 1955-06-27 DE DE1955E0010924 patent/DE1001258C2/en not_active Expired
- 1955-06-30 CH CH336063D patent/CH336063A/en unknown
- 1955-06-30 GB GB18885/55A patent/GB786104A/en not_active Expired
- 1955-06-30 FR FR1211308D patent/FR1211308A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1211308A (en) | 1960-03-15 |
| CH336063A (en) | 1959-02-15 |
| DE1001258B (en) | 1957-01-24 |
| DE1001258C2 (en) | 1957-07-04 |
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