GB811697A - Improvements in the production of compounds of the vitamin-a series - Google Patents
Improvements in the production of compounds of the vitamin-a seriesInfo
- Publication number
- GB811697A GB811697A GB18642/57A GB1864257A GB811697A GB 811697 A GB811697 A GB 811697A GB 18642/57 A GB18642/57 A GB 18642/57A GB 1864257 A GB1864257 A GB 1864257A GB 811697 A GB811697 A GB 811697A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vitamin
- ester
- acid
- zinc
- methylsorbic
- 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
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds of the Vitamin A series are obtained by condensing b -ionone with an e - halo - b - methylsorbic acid ester of the formula: <FORM:0811697/IV (b)/1> (wherein X is a halogen atom, e.g. a bromine atom, and COOR is a carboxylic acid ester group, R being e.g. an alkyl radical having 1 to 4 carbon atoms or a benzyl or hexyl group) in the presence of an active metal such as magnesium, zinc, cadmium or lithium (preferably zinc), splitting off water from the resulting hydroxy-ester of formula: <FORM:0811697/IV (b)/2> and, if desired, reducing the Vitamin A acid ester thus obtained to the Vitamin A alcohol. The esters are obtained as mixtures of stereoisomers (the ratio depending on the dehydration method used), which may be interconverted by the usual methods. In an example, b -ionone is condensed in tetrahydrofuran with e -bromo-b -methyl-sorbic acid ethyl ester in the presence of iodine-activated zinc, and the resulting hydroxy-ester is dehydrated by heating in benzene with p-toluenesulphonic acid. It is stated that the mainly trans-Vitamin A ester so formed may be saponified to all-trans-Vitamin A acid, or reduced, e.g. with calcium aluminium hydride to Vitamin A alcohol. e - Bromo - b - methylsorbic acid is obtained by the action of phosphorus tribromide on the corresponding hydroxy compound.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE811697X | 1956-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB811697A true GB811697A (en) | 1959-04-08 |
Family
ID=6728389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18642/57A Expired GB811697A (en) | 1956-06-14 | 1957-06-13 | Improvements in the production of compounds of the vitamin-a series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB811697A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004037213A2 (en) * | 2002-10-24 | 2004-05-06 | The Procter & Gamble Company | Nuclear hormone receptor compounds, products and methods employing same |
-
1957
- 1957-06-13 GB GB18642/57A patent/GB811697A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004037213A2 (en) * | 2002-10-24 | 2004-05-06 | The Procter & Gamble Company | Nuclear hormone receptor compounds, products and methods employing same |
| WO2004037213A3 (en) * | 2002-10-24 | 2004-07-29 | Procter & Gamble | Nuclear hormone receptor compounds, products and methods employing same |
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