http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1004959-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c7ad58d3c0b071069a8ee0cb8c8ba2e8 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C67-343 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C51-09 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C67-293 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C51-09 |
| filingDate | 1964-02-07-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1965-09-22-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1004959-A |
| titleOfInvention | Process for the production of cis, trans-conjugated dienes |
| abstract | Cis, trans-conjugated dienes of general formula <FORM:1004959/C2/1> where R represents -COO-alkyl, -COOH, -CH2OH or -CH2O Acyl, m is 0 to 12, and n 4 to 12, and m + n 4-16 are prepared by reacting a triaryl phosphonium halide, [Ar3P-CH2-(CH2)n-R1]+X-where Ar is a phenyl radical, R1 is -COO Alkyl or -CH2O Acyl, and X is Cl, Br or I with a proton acceptor to produce a phosphorane Ar3P = CH-(CH2)n-R1 and reacting with an aldehyde <FORM:1004959/C2/2> If R1 represents -COO Alkyl the acid R1= -COOH is prepared by alkaline hydrolysis, and the alcohol -CH2OH, is then prepared by reduction with a complex metal hydride, e.g. lithium aluminium hydride, or alternatively by direct reduction or alkaline hydrolysis of the compounds when R1 is -COO Alkyl, and -CH2OAcyl respectively. The reaction takes place at a temperature of between - 10 DEG C. and 40 DEG C., preferably in an anhydrous solvent, with an alkali metal or alkaline earth metal alkoxide or amide as proton acceptor. The products are purified by fractional distillation and the trans-trans dienes separated from the product by fractional crystallization, or in the form of urea or thiourea addition compounds. Examples describe the preparation of 10-cis, 12-trans hexadecadiene-1-oic acid, alcohol, and methyl ester, 11-cis, 13-trans-heptadecadiene-1-oic acid, alcohol and methyl ester, pentadeca-11,13-diene-1-oic acid methyl ester, 10-cis, 12-trans-tetradecadiene-1-ol, 10 - cis, 12 - trans - octadecadien-1-ol, and octadeca - 10,12 - diene - 1 - oic acid methyl ester, 9 - cis,11 - trans - pentadecadien - 1 - ol and pentadeca - 9,11 - diene - 1 - oic acid ethyl ester. The cis,trans-diene products are used as insect attractants and exhibit an anticatabolic activity. The triaryl phosphonium halides of general formula [ArP = CH-(CH2)n-R1](+)X(-), are prepared by reacting a triaryl phosphine with the halogen compounds X-CH2-(CH2)n -CH2O acyl and X-CH2-(CH2)n-CH2-COO alkyl at an elevated temperature in the presence of a solvent such as benzene, toluene, xylene, or dimethylformamide, and examples describe the preparation of [9-carbomethoxynonyl]-triphenyl phosphonium iodide, [10-carbomethoxy - decyl] - triphenyl phosphonium iodide, and [10 - acetoxy - decyl - triphenyl phosphonium bromide. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2005087017-A2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2005087017-A3 |
| priorityDate | 1963-02-08-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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