GB774462A - Novel unsaturated esters ethers and aldehydes and a process for the manufacture thereof - Google Patents
Novel unsaturated esters ethers and aldehydes and a process for the manufacture thereofInfo
- Publication number
- GB774462A GB774462A GB20261/55A GB2026155A GB774462A GB 774462 A GB774462 A GB 774462A GB 20261/55 A GB20261/55 A GB 20261/55A GB 2026155 A GB2026155 A GB 2026155A GB 774462 A GB774462 A GB 774462A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexen
- trimethyl
- ether
- methylmalonyl
- dialdehyde
- 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
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
-
- 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
- C07C403/14—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 doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 1-esters and 1-ethers of 1,3,6-trihydroxy-2,6-dimethyl-8-[21, 61, 61-trimethyl - cyclohexen - 11 - yl] - octadien - 1,7 - yne - 4, 2,6 - dimethyl - 8 - [21,61,61 - trimethyl-cyclohexen - 21 - ylidene] - octadien - 2,6 - yn - 4 - al - 1, 2,6 - dimethyl - 8 - [21,61,61 - trimethyl-cyclohexen-21-ylidene]-octatriene-2,4,6-al-1 and a process of condensing 3-hydroxy-3-methyl-5-[21,61,61 - trimethyl - cyclohexen - 11 - yl] - penten - 4 - yne - 1 with an ester or ether of 3 - hydroxy - 2 - methyl - propen - 2 - al - 1 in an organo-alkali metal or Grignard reaction to produce said 1-esters and 1-ethers, and, if desired, converting the 1-ester or 1-ether to an aldehyde by treatment with an acid agent and selective hydrogenation of the product. The organo alkali-metal reaction may be effected using phenyl-lithium in diethyl ether or lithium amide or sodamide in liquid ammonia. The conversion of the 1-ester or 1-ether to the acetylenicaldehyde may be effected in aqueous acetone with sulphuric acid. The selective hydrogenation may be effected in the presence of a small quantity of quinoline and of a palladium lead catalyst. Starting compounds. 3-Hydroxy-3-methyl-5-[21,61,61 - trimethyl - cyclohexen - 11 - yl] - penten-4-yne-1 is obtained by condensing b -ionone with lithium acetylide in liquid ammonia; 3-hydroxy - 2 - methyl - propen - 2 - al - 1 is obtained by reacting the sodium salt methylmalonyl dialdehyde with an acid chloride in an inert water-free solvent or by reacting methylmalonyl dialdehyde with an alcohol at an elevated temperature; the sodium salt of methylmalonyl dialdehyde is obtained by condensing a propenyl ether with ortho-formic acid ethyl ester to form the tetraethyl acetal of methylmalonyl dialdehyde, which is subsequently hydrolysed and neutralised with caustic soda.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH774462X | 1954-07-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB774462A true GB774462A (en) | 1957-05-08 |
Family
ID=4535697
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20261/55A Expired GB774462A (en) | 1954-07-16 | 1955-07-13 | Novel unsaturated esters ethers and aldehydes and a process for the manufacture thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB774462A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3091631A (en) * | 1957-10-18 | 1963-05-28 | Hoffmann La Roche | Production of acetylenic carotenoid aldehydes and acetal intermediates therefor |
US4092366A (en) * | 1975-04-10 | 1978-05-30 | Scm Corporation | Synthesis of Vitamin A, intermediates and conversion thereof to Vitamin A |
-
1955
- 1955-07-13 GB GB20261/55A patent/GB774462A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3091631A (en) * | 1957-10-18 | 1963-05-28 | Hoffmann La Roche | Production of acetylenic carotenoid aldehydes and acetal intermediates therefor |
US4092366A (en) * | 1975-04-10 | 1978-05-30 | Scm Corporation | Synthesis of Vitamin A, intermediates and conversion thereof to Vitamin A |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB774462A (en) | Novel unsaturated esters ethers and aldehydes and a process for the manufacture thereof | |
GB523449A (en) | Production of ethers containing fluorine | |
GB788301A (en) | A process for the manufacture of 6, 10-dimethyl-undecanone-(2) | |
Kipnis et al. | 2-Substituted tetrahydropyranyl sulfides | |
GB936892A (en) | Improvements in or relating to d-homo-18-nor-androstenes | |
GB953775A (en) | Processes for the preparation of sorbic acid and alkyl esters of sorbic acid | |
GB935006A (en) | Improvements in or relating to isoprene derivatives of trimethyl cyclohexene | |
GB786349A (en) | Novel unsaturated alcohols and a process for the manufacture thereof | |
GB788302A (en) | The manufacture of geranyl-acetone and dihydrogeranyl-acetone and of hexahydro-pseudoionone therefrom | |
GB769260A (en) | Process for the preparation of isomeric racemic dihydrolysergic acids and their homologues | |
GB772199A (en) | A process for the manufacture of -a,-ß-unsaturated carboxylic acids and esters thereof | |
US2779792A (en) | Hoxchsxchxo | |
GB838569A (en) | Alkenoic acids | |
GB761974A (en) | Isomorphinane derivatives | |
GB736074A (en) | Process for the manufacture of butyraldehyde | |
GB789247A (en) | Novel unsaturated alcohols and a process for the manufacture thereof | |
GB959126A (en) | Process for the production of 4-[2,6,6-trimethylcyclohex-1-enyl]-2-methyl-but-3-en-1-al | |
GB987433A (en) | Process for the manufacture of tetracyclic compounds | |
GB585316A (en) | Improvements in or relating to the purification of capryl alcohol | |
GB1105168A (en) | Process for the conversion of acrolein and methacrolein into the corresponding unsaturated alcohols | |
GB761091A (en) | Process for the production of thiobarbiturates | |
GB785086A (en) | Novel unsaturated ketones and a process for the manufacture thereof | |
GB765516A (en) | Novel unsaturated alcohols and esters and a process for preparation of same | |
GB786350A (en) | Novel unsaturated ketones and a process for the manufacture thereof | |
GB1389177A (en) | Process for the simi-hydrogenation of citral and its homologues to give citronellal and homologues of citronellal |