GB802138A - Novel diones and a process for the manufacture of same - Google Patents
Novel diones and a process for the manufacture of sameInfo
- Publication number
- GB802138A GB802138A GB5659/58A GB565958A GB802138A GB 802138 A GB802138 A GB 802138A GB 5659/58 A GB5659/58 A GB 5659/58A GB 565958 A GB565958 A GB 565958A GB 802138 A GB802138 A GB 802138A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimethyl
- dione
- yne
- tetramethyl
- acid
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises 1,18-disubstituted-3,7,12,16 - tetramethyl - octadecaheptaene - 2,4,7,9,11,14,16 - dione - 6,13's and the corresponding octadecahexaen - 2,4,7,11,14,16 - yne - 9-dione-6,13's, wherein each of the said substituents is 2,6,6-trimethyl-cyclohexylidene (which may contain oxo or hydroxy or acyloxy group as a substituent in the 4-position) or 2,6,6-trimethyl-cyclohexen-1-yl (which may contain a hydroxy or acyloxy group as a substituent in the 4-position) or 2,6,6-trimethyl-cyclohexadien-1,3-yl or 2,6,6-trimethyl-hexen-5-xylidene and the preparation thereof which comprises bilaterally condensing in the presence of an acidic condensing agent a 3,8-dimethyl-2,9-dialkoxy-decapentaene - 1,3,5,7,9 or the correspondingly substituted decatetraene - 1,3,7,9 - yne - 5 with a 1,1 - dialkoxy - 2 - methyl - 4 - substituted - butene-2 in which the substituent is a 2,6,6-trimethylcyclohexylidene (which may contain an oxo or hydroxy or acyloxy group as a substituent in the 4-position) or 2,6,6-trimethyl-cyclohexen-1-yl (which may contain a hydroxy or acyloxy group in the 4-position) or 2,6,6-trimethyl-cyclohexadien-1,3-yl or 2,6,6-trimethyl-hexen-5-ylidene, and hydrolysing the resulting 1,18-di-substituted - 3,7,12,16 - tetramethyl - 4,6,6,13,13,15 - hexa-alkoxy - octadecapentaene - 2,7,9,11,16 or correspondingly substituted octadecatetraene - 2,7,11,16 - yne - 9 in the presence of an acid. The condensation may be effected in an inert solvent between 15-50 DEG C. As condensing agents there may be used boron trifluoride etherate, zinc chloride, titanium tetrachloride, ferric chloride or tin tetrachloride. Hydrolysis of the condensation product may be carried out in water-soluble organic or inorganic acids, e.g. p-toluene sulphonic acid, acetic acid, propionic acid, oxalic acid, sulphuric acid and phosphoric acid or in the presence of water-soluble metal salts having an acid reaction, e.g. zinc chloride or sodium bisulphate. Examples describe the preparation of 1,18-di-[21,61,61-trimethyl - cyclohexen 8 11 - yl] - 3,7,12,16 - tetramethyl - octadecahexaene - 2,4,7,11,14,16 - yn - 9 - dione - 6,13, the corresponding octadecaheptaene - 2,4,7,9,11,14,16 - dione - 6,13, 1,18-di - [21,61,61 - trimethyl - 41 - oxo - cyclohexylidene] - 3,7,12,16 - tetramethyl - octadecahexaene - 2,4,7,11,14,16 - yne - 9 - dione - 6,13,1,18 - di - [21,61,61 - trimethyl - 41 - acetoxy - cyclohexen - 11 - yl] - 3,7,12,16 - tetramethyl - octadecahexaene - 2,4,7,11,14,16 - yne - 9 - dione - 6,13, and 1,18 - di - [21,61,61 - trimethylcyclohexadien - 11,31 - yl] - 3,7,12,16 - tetramethyl - octadecahexaene - 2,4,7,11,14,16 - yne - 9 - dione - 6,13. Specification 802,137 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH802138X | 1955-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB802138A true GB802138A (en) | 1958-10-01 |
Family
ID=4537735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5659/58A Expired GB802138A (en) | 1955-08-31 | 1956-08-29 | Novel diones and a process for the manufacture of same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB802138A (en) |
-
1956
- 1956-08-29 GB GB5659/58A patent/GB802138A/en not_active Expired
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