Synthesis of triconjugated dienones and intermediates used in sa

Details Synthesis of triconjugated dienones and intermediates used in sa Synthesis of triconjugated dienones and intermediates used in sa

1983-11-14

1985-12-24

Garner, Vivian

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

131276, 25217411, 252522R, 252522A, 252 86, 424 69, 560266, 568314, 568335, 568388, 568417, C07C 69157

Patent

active

045607915

ABSTRACT:
Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.5 alkyl in the presence of an aluminum chloride catalyst and a methylene dichloride solvent in order to form the novel intermediate genus defined according to the structure: ##STR4## then dehydrohalogenating the compound defined according to the structure: ##STR5## using an alkali metal carbonate and a dimethylformamide solvent in order to form the novel compound genus having the structure: ##STR6## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and then dehydroacyloxylating the compound having the structure: ##STR7## in order to form the compound having the structure: ##STR8## the dehydroacyloxylation step taking place in the presence of an akali metal carbonate and dimethylformamide solvent.

REFERENCES:
patent: 1737203 (1929-11-01), Schoeller et al.
patent: 2223885 (1940-12-01), Buchman
patent: 4346237 (1982-08-01), Boden

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