GB495887A - Improvements relating to the production of alcohols of the cyclopentanopolyhydrophenanthrene series - Google Patents
Improvements relating to the production of alcohols of the cyclopentanopolyhydrophenanthrene seriesInfo
- Publication number
- GB495887A GB495887A GB1686837A GB1686837A GB495887A GB 495887 A GB495887 A GB 495887A GB 1686837 A GB1686837 A GB 1686837A GB 1686837 A GB1686837 A GB 1686837A GB 495887 A GB495887 A GB 495887A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cholestanol
- sulphonic acid
- ester
- saponified
- glacial acetic
- 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
Landscapes
- Steroid Compounds (AREA)
Abstract
Trans-alcohols of the cyclopentanopolyhydrophenanthrene series are converted into compounds which are their isomers in respect of the steric position of the hydroxyl group, by saponifying a sulphonic acid ester of the alcohol, if desired after previous re-esterification. Parent materials for the process of the invention mentioned include the sulphonic acid esters of sterols, and in particular cholestanols and coprosterol; androsterones, androstanediols, androstane-17-ol-3 ones, hexahydro-oestradiols, oxy - bisnorcholanic acids, oxy - aetiocholanic acids, pregnanolones, and pregnanediols. The sulphonic acid esters may be conveniently prepared by the action of a sulphonic acid halide on the hydroxy compound or by the action of a sulphonic acid salt on a halide of the cyclopentanopolyhydrophenanthrene series. The saponification is preferably conducted by prolonged heating with alkali hydroxide in aqueous or alcoholic solution. In cases where re-esterification is used, it is preferred to heat the sulphonic acid ester with an organic carboxylic acid in glacial acetic acid solution, and then saponify the ester so produced. In examples: (1) cholestanol-para-toluene sulphonic acid is saponified with alcoholic caustic soda to give epi-cholestanol. The methane sulphonic ester may be substituted for the p-toluene sulphonic ester; (2) cholestanol-p-toluene sulphonic acid ester is saponified with N-sulphuric acid to give epi-cholestanol; (3) a glacial acetic acid solution of cholestanol-p-toluene sulphonic acid ester is heated for 10 hours in the presence of sulphuric acid, and the sulphur-free product saponified with alcoholic caustic soda to give epi-cholestanol; (4) a glacial acetic acid solution of cholestanol methane sulphonic acid ester is heated with potassium acetate for 60 hours and the sulphur free product saponified with alcoholic caustic soda to give epi-cholestanol; (5) transandrosterone-p-toluene sulphonic acid ester is heated in glacial acetic acid solution with potassium acetate for 4 hours, and the cisandrosterone acetate so produced is saponified with alkali to give cis-androsterone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1686837A GB495887A (en) | 1937-06-17 | 1937-06-17 | Improvements relating to the production of alcohols of the cyclopentanopolyhydrophenanthrene series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1686837A GB495887A (en) | 1937-06-17 | 1937-06-17 | Improvements relating to the production of alcohols of the cyclopentanopolyhydrophenanthrene series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB495887A true GB495887A (en) | 1938-11-22 |
Family
ID=10085122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1686837A Expired GB495887A (en) | 1937-06-17 | 1937-06-17 | Improvements relating to the production of alcohols of the cyclopentanopolyhydrophenanthrene series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB495887A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5062513A (en) * | 1988-11-11 | 1991-11-05 | Fichtel & Sachs Ag | Hub guidance for friction clutch |
-
1937
- 1937-06-17 GB GB1686837A patent/GB495887A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5062513A (en) * | 1988-11-11 | 1991-11-05 | Fichtel & Sachs Ag | Hub guidance for friction clutch |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB495887A (en) | Improvements relating to the production of alcohols of the cyclopentanopolyhydrophenanthrene series | |
| GB541782A (en) | Improvements in the manufacture of brominated aromatic carboxylic acids | |
| US2239012A (en) | Compounds of the cyclopentanopoly-hydrophenanthrene series and process of making same | |
| Linstead et al. | 243. Elimination reactions of esters. Part I. The formation of αβ-unsaturated acids from β-acyloxy-compounds | |
| US2254407A (en) | Acids of the cyclopentano polyhydro phenanthrene series and their derivatives and a method of producing the same | |
| GB491799A (en) | Manufacture of derivatives of cyclopentano-polyhydrophenanthrene | |
| GB715545A (en) | Phenyl cyclohexanes and cyclohexenes | |
| GB453789A (en) | A process of synthetically preparing ª‰(10)-oxycamphor | |
| GB442319A (en) | Process for the production of pregnanolones | |
| GB516056A (en) | Manufacture of compounds of the cyclopentanopolyhydrophenanthrene series | |
| US2306552A (en) | Process for the manufacture of ketols of the cyclopentanopolyhydrophenanthrene series and derivatives thereof | |
| GB497544A (en) | An improved process for working up the residues obtained in the distillation of levulinic acid | |
| GB468025A (en) | Process for the manufacture of reduction products derived from dehydroandrosterone | |
| GB471803A (en) | A process for separating stereoisomeric alcohols of the androstane series | |
| US3109008A (en) | Process for the preparation of 16-keto-18-nor-steroids | |
| GB763945A (en) | Process for the preparation of etiocholenic acid derivatives | |
| GB415472A (en) | Improvements in or relating to the manufacture of oxalic acid and esters thereof | |
| GB341654A (en) | A process for preparing pure inactive menthol | |
| GB483670A (en) | Process for the manufacture of hydroxy acids and unsaturated acids of the cyclopentanophenanthrene series | |
| GB453812A (en) | A process of synthetically preparing ª‰(10)-oxycamphor | |
| GB455018A (en) | Process for the manufacture of esters of polycyclic alcohols | |
| GB302750A (en) | Improvements in the manufacture of acyl derivatives of beta-ketonic esters and beta-diketones | |
| GB488814A (en) | Process for the manufacture of polyhydric alcohols of the cyclopentano-polyhydrophenanthrene series | |
| GB736974A (en) | Process for the separation of some aromatic acids and esters | |
| GB516542A (en) | Manufacture of cyclopentanopolyhydrophenanthrene derivatives |