http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-857456-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_1a8baad16b07a61c3dad8f3df460394c |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C43-178 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C43-215 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C41-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C41-01 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C43-15 |
| filingDate | 1957-05-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1960-12-29-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-857456-A |
| titleOfInvention | Preparation of derivatives of unsaturated terpene hydrocarbons |
| abstract | A process for producing a tertiary allyl ether of the pinane and p-menthane series comprises treating an alpha pinene or an unsaturated hydrocarbon compound of the p-menthane series having as the sole cyclic double bond a carbon-carbon double bond involving the cyclic carbon atom carrying the methyl group and possessing a cyclic methylenic carbon atom alpha to the cyclic double bond and beta with respect to the cyclic carbon atom carrying the methyl group, with molecular chlorine in the presence of an alcohol containing up to three carbon atoms until not more than one mole of chlorine per mole of material being treated is reacted whereby a vicinal chloro-ether derivative of the starting material is formed in which the ether group is attached to the tertiary carbon atom originally involved in the double bond and then dehydrochlorinating the chloro-ether, preferably in situ, by treatment with an alkaline material to form an allylic tertiary ether. The invention also includes 1-alkoxy-2-p-menthenes, 1-alkoxy-2, 8-p-menthadienes, 1-alkoxy, 2-p-menthene-8-ols, 1-alkoxy-2-pinenes, 1-alkoxy-2-chloro-p-menthanes,1-alkoxy-2-chloro-8-p-menthenes, 1-alkoxy-2-chloro-p-menthene-8-ols, and 1-alkoxy-2-chloro-pinanes in which the alkoxy radical contains up to 3 carbon atoms. The chlorination is preferably carried out at 15 DEG C.-20 DEG C. in the presence of sodium bicarbonate and the dehydrochlorination by heating the chloroether in diethylene glycol in the presence of potassium hydroxide at about 200 DEG C. Examples describe the conversion of d-carvomenthene (prepared by hydrogenation of d-limonene) to 1-methoxy-2-chloro-p-menthane with some 6-chloro- and 6-methoxy-1-p-mehthene and then to 1-methoxy-2-p-menthene; of d-limonene to 1-methoxy-2-chloro-8-p-menthene with some 6-chloro-and 6-methoxy-1, 8-p-menthadiene and then to 1-methoxy-2, 8-p-menthadiene with some 1-methoxy-2-chloro-8-p-methene; of a -pinene to 1-methoxy-2-chloro-pinane with some pinocarvyl chloride, pinocarvyl methyl ether and myrtenyl methyl ether, and then to 1-methoxy-2-pinene; of a -terpineol to 1-methoxy-2-chloro-p-menthene-8-ol with some 6-methoxy-and 6-chloro-1-p-menthene-8-ol, and then to 1-methoxy-2-p-menthene-8-ol and 1-methoxy-2, 8-epoxy-p-menthane; and of a -carvomenthene to 1-ethoxy-and 1-isopropoxy-2-chloro-p-menthane. Details are given of the identification of products and by-products by I.R. spectra, hydrolysis, oxidation and hydrogenation. |
| priorityDate | 1957-05-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 71.