GB782316A - Unsaturated compounds and the manufacture thereof - Google Patents
Unsaturated compounds and the manufacture thereofInfo
- Publication number
- GB782316A GB782316A GB22285/55A GB2228555A GB782316A GB 782316 A GB782316 A GB 782316A GB 22285/55 A GB22285/55 A GB 22285/55A GB 2228555 A GB2228555 A GB 2228555A GB 782316 A GB782316 A GB 782316A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexen
- trimethyl
- dimethyl
- tetramethyl
- reacting
- 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
- C07C403/24—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 six-membered non-aromatic rings, e.g. beta-carotene
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
The invention comprises 1-[21,61,61-trimethyl cyclohexen - 11 - yl - 11] - 18 - [211,611,611 - trimethyl - cyclohexen - 211 - yl - 111] - 3,7,12,16-tetramethyl - octadecaoctaene - (1,3,5,7,11,13, 15,17) - ine - 9, 9,10 - mono - cis - 1 - [21,61,61-trimethyl - cyclohexen - 11 - yl - 11] - 18 - [211, 611,611 - trimethyl - cyclohexen - 211 - yl - 111] - 3,7,12,16 - tetramethyl - octadecanonaene - (1,3,5,7,9,11,13,15,17), crystalline all-trans-DL-a -carotene and the preparation thereof by reacting 10 - [21,61,61 - trimethyl - cyclohexen - 11 - yl - 11] - 4,8 - dimethyl - decatrien - 4,6,8 - in-1 - ol - 3 with 8 - [21,61,61 - trimethyl - cyclohexen - 21 - yl - 11] - 2,6 - dimethyl - octatrien - 2,4,6 - ol - 1 - with a hydrocarbon magnesium halide or hydrocarbon-(alkali metal), hydrolysing the reaction product thereby produced, subjecting the 1-[216161-trimethyl-cyclohexen-11-yl -11] - 18 - [211,611,611 - trimethyl - cyclohexen - 211 yl - 111] - 3,7,12,16 - tetramethyl - octadecahexaene - (2,4,6,12,14,16) - ine - 9 - diol - 8,11 to dehydration with the aid of an anionotropic dehydration agent so as to eliminate both the hydroxyl group and effect allyl rearrangement, hydrogenating the 1-[21,61,61-trimethyl-cyclohexen - 11 - yl - 11] - 18 - [211,611,611 - trimethyl - cyclohexen - 211 - yl - 111] - 3,7,12,16 - tetramethyl - octadecaoctaen - (1,3,5,7,11,13,15,17) - ine formed with about one molar proportion of hydrogen in the presence of an inhibited hydrogenation catalyst and maintaining the resulting 9,10-mono-cis 1-[21,61,61-trimethyl-cyclohexen-11 - yl - 11] - 18 - [211,611,611 - trimethyl - cyclohexen - 211 - yl - 111] - 3,7,12,16 - tetramethyloctadecanenaene - (1,3,5,7,9,11,13,15,17) under isomerization conditions for a sufficient time to substantially convert same to all-trans-DL-a -carotene. The first addition step may be effected with alkyl magnesium bromide or chloride, or lithium methyl or lithium phenyl, the dehydration with p-toluenesulphonic acid and the hydrogenation in the presence of a leadpoisoned palladium catalyst. The fourth stage isomerization may be effected by iodine in an inert solvent, by heating or by irradiation. The starting compound 8-[21,61,61-trimethylcyclohexen - 21 - yl - 11] - 2,6 - dimethyl - octatrien-2,4,6-al-1 is obtained by reacting 4-[21,61,61-trimethyl - cyclohexen - 21 - yl - 11] - 2 - methyl - buten-2-al-1 with g -bromo tiglic acid ethyl ester, dehydrating the product to give 8-[21,61,61-trimethyl - cyclohexen - 21 - yl - 11] - 2,6 - dimethyloctatriene - 2,4,6 - oic - 1 acid ethyl ester, hydrogenating the latter to produce a carbinol group and oxidizing the carbinol group to give the required aldehyde and 10-[21,61,61-trimethyl cyclohexen - 11 - yl - 11] - 4,8 - dimethyl - decatriene - in - 1 - ol - 3 is obtained by reacting 8 - [21,61,61 - trimethyl - cyclohexen - 11 - yl - 11]-2,6 - dimethyl - octatriene - 2,4,6 - al - 1 with an alkali metal or alkaline earth metal acetylide and hydrolysing the reaction product.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH782316X | 1954-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB782316A true GB782316A (en) | 1957-09-04 |
Family
ID=4536323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22285/55A Expired GB782316A (en) | 1954-08-04 | 1955-08-03 | Unsaturated compounds and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB782316A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008122988A1 (en) * | 2007-04-05 | 2008-10-16 | Cadila Healthcare Limited | Process for preparation of atovaquone and the conversion of cis-isomer to trans- isomer |
-
1955
- 1955-08-03 GB GB22285/55A patent/GB782316A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008122988A1 (en) * | 2007-04-05 | 2008-10-16 | Cadila Healthcare Limited | Process for preparation of atovaquone and the conversion of cis-isomer to trans- isomer |
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