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

1984-06-13

1985-12-24

Reamer, James H.

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

Organic compounds

Oxygen containing

560266, 560262, C07C 4565

Patent

active

045608024

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 dehydrocyloxylating 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 alkali metal carbonate and dimethylformamide solvent.

REFERENCES:
patent: 1737203 (1929-11-01), Scholler et al.
patent: 2006198 (1935-06-01), Frolich et al.
patent: 2194704 (1940-03-01), Kroeger
patent: 4346237 (1982-08-01), Boden
Adams et al, J. Chem. Soc., Perkin I, 1975, pp. 1741-1743.
Thomas, Anhydrous Aluminum Chloride in Organic Chemistry, pp. 752-757, (1941).
Young, "Protective Groups in Organic Chemistry", pp. 309-321, (1973).
Fieser et al, Reagents for Organic Synthesis, vol. 4, pp. 414-415, (1978).

Affiliated with

Also associated with

Rating

Synthesis of triconjugated dienones and novel intermediates used does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of triconjugated dienones and novel intermediates used, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of triconjugated dienones and novel intermediates used will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1480359