GB816256A - Improvements in or relating to methods of reducing unsaturated compounds - Google Patents
Improvements in or relating to methods of reducing unsaturated compoundsInfo
- Publication number
- GB816256A GB816256A GB4595/57A GB459557A GB816256A GB 816256 A GB816256 A GB 816256A GB 4595/57 A GB4595/57 A GB 4595/57A GB 459557 A GB459557 A GB 459557A GB 816256 A GB816256 A GB 816256A
- Authority
- GB
- United Kingdom
- Prior art keywords
- metal
- ammonium
- compound
- esters
- aliphatic
- 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
-
- 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
-
- 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
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A compound having the general formula <FORM:0816256/IV (b)/1> wherein R1 designates an hydrogen atom or an aliphatic or aromatic acyl radical and R designates a saturated or unsaturated aliphatic hydrocarbon radical is obtained by reducing an unsaturated compound of the general formula <FORM:0816256/IV (b)/2> wherein R and R1 are as defined above, with an alkali-metal or alkaline earth metal in liquid ammonia, decomposing the reaction product by means of a substance which under the reaction conditions replaces a metal atom by an hydrogen atom to obtain the desired compound which is separated from the reaction mixture. Esters which may be employed as starting compounds are those of acetic acid, propionic acid, butyric acid, benzoic acid or o-nitro-benzoic acid. Suitable solvents are mono-ethers such as dimethyl, diethyl, methylethyl, or methylbutyl ether, aliphatic hydrocarbons, for example n-hexane or n-heptane, or mixtures such as mixtures of cyclohexane with diethyl ether, of cyclohexane with dimethylether, and of benzene or toluene with dimethyl or diethylether. As alkali and alkaline earth metals there may be used lithium, sodium, potassium or calcium. The reaction between the metal and the compound to be reduced in liquid ammonia is best performed in a homogeneous system. Prior to decomposition of the metal compound, excess metal may be oxidized by means of sodium, calcium or ammonium nitrates, bromates or iodates. Decomposition may be effected with the ammonium salts of strong acids such as ammonium chloride, ammonium bromide, ammonium sulphate and ammonium nitrate, or water or aliphatic alcohols such as methanol, ethanol, propanol, butanol or tertiary amyl alcohol. Purification of the reduction mixture is carried out by chromatographic methods, or by esterification and crystallization. Examples describe in detail the production of dihydrotachysterol-2, dihydrotachysterol-3 and their esters from ergocalciferol, cholecalciferol and their esters.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL816256X | 1956-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB816256A true GB816256A (en) | 1959-07-08 |
Family
ID=19838885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4595/57A Expired GB816256A (en) | 1956-02-14 | 1957-02-11 | Improvements in or relating to methods of reducing unsaturated compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB816256A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0603726A2 (en) * | 1992-12-21 | 1994-06-29 | Bristol-Myers Squibb Company | Nutritional compositions containing vitamin d esters |
-
1957
- 1957-02-11 GB GB4595/57A patent/GB816256A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0603726A2 (en) * | 1992-12-21 | 1994-06-29 | Bristol-Myers Squibb Company | Nutritional compositions containing vitamin d esters |
| EP0603726B1 (en) * | 1992-12-21 | 2002-04-17 | Bristol-Myers Squibb Company | Nutritional compositions containing vitamin d esters |
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