Synthesis of triconjugated dienones and novel intermediates used

Details Synthesis of triconjugated dienones and novel intermediates used Synthesis of triconjugated dienones and novel intermediates used

1984-08-17

1986-11-18

Lone, Werren B.

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

Organic compounds

Carboxylic acid esters

252522R, 568335, 568338, 560254, 560266, C07C 69145, C07C 69157

Patent

active

046237496

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 with a substituted or unsubstituted prenyl ester having the structure: ##STR2## 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 a halogen-ester intermediate defined according to the structure: ##STR3## then dehydrohalogenating said halogen-ester intermediate using an alkali metal carbonate and a dimethylformamide solvent in order to form a ketoester having the structure: ##STR4## 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 ketoester in the presence of an alkali metal carbonate and dimethylformamide solvent in order to form the triconjugated dienone.

REFERENCES:
Braude et al, Chem. Abstracts, 49: 3121e, 1955.

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