http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-907431-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_b75b73e966a8d4daf619324117f166e9 http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_f4c674f2c4b715cbb0efb5847ad34df0 http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_54471a85c2a36f593d0cc781adf41bf2 http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c319ad0d27597ce8ed02b3eaa0ae01af |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C45-68 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C45-63 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C45-455 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C45-63 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C45-45 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C45-68 |
| filingDate | 1961-02-24-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1962-10-03-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-907431-A |
| titleOfInvention | Improvements in or relating to alicyclic keto-esters and process for their manufacture |
| abstract | The invention comprises compounds of the general formula <FORM:0907431/IV (b)/1> wherein R1 represents a methyl or ethyl group, R represents an alkyl radical containing 4 to 6 carbon atoms and n represents 1 or 2; and a process for their preparation by condensing a 2-alkyl-2-cyclo-pentene or hexene-1 one with a lower dialkyl malonate in the presence of a basic condensing agent, saponifying and decarboxylating the resulting dialkyl-2-alkyl-3-oxo-cycloalkyl malonate and esterifying the resulting 2-alkyl-3-oxo-cycloalkyl acetic acid to give the desired methyl or ethyl ester. The process is preferably effected by condensing the ketone and malonate in the presence of sodium ethoxide, heating the resulting adduct with a mixture of acetic and hydrochloric acids to effect saponification and decarboxylation and esterifying the resulting acid with the appropriate alcohol. Examples describe the preparation of the methyl and ethyl esters of 2-n-butyl-, n and iso-amyl- and n-hexyl-3-oxo-cyclopentyl acetic acid and 2-n-amyl 3-oxo-cyclohexyl acetic acid. 2-iso-amyl-2-cyclopentene-1-one is prepared by reacting cyclopentane - 1,2 - dione - isobutyl enol ether with iso amyl magnesium bromide and heating the product with polyphosphonic acid. The n-butyl and n-hexyl compounds may be similarly prepared. The n-hexyl compound may also be prepared by selective chlorination and dehydrochlorination of 2-n-hexyl cyclopentanone. The n-amyl compound may also be prepared by cyclodehydration of g -decalactone. 2-n-butyl-, n-pentyl-, iso-pentyl and n-hexyl-2-cyclohexene-1-ones may be prepared cyclising the corresponding ethyl d -oxoalkanoate according to the Dieckmann method to give the 2-alkyl-cyclohexane-1,3-dione, chlorinating the diketone with PCl3 to give the 2-alkyl-3-chloro-2-cyclohexene-1-one and reducing the latter by means of zinc and potassium iodide. Ethyl d -oxo-9-methyl decanoate (used in the preparation of the isopentyl compound) may be prepared by condensing isohexyl methyl ketone with diethyl carbonate, condensing the resulting ethyl b -oxo-7-methyl octoate with methyl acrylate to give methyl g -carbethoxy-g -oxo-9-methyl decanoate, saponifying and decarboxylating the latter to give d -oxo-9-methyl-decanoic acid and esterifying the acid.ALSO:Perfume compositions comprise as an odour-modifying agent or as an odoriferous ingredient a cycloaliphatic keto ester of the general formula <FORM:0907431/VI/1> wherein R1 represents a methyl or ethyl group, R represents an alkyl radical containing 4-6 carbon atoms and n represents 1 or 2. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4629805-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4614831-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4643903-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4668817-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4537704-A |
| priorityDate | 1960-02-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 61.