4,7-Dioxooctanoic acid from the acid catalysed reaction of (E)-4-(2-furyl)but-3-enone. Electrochemical hydrogenation of some furan derivatives

Abstract

A two phase acidic reaction medium has been developed for the conversion of (E)-4-(2-furyl)but-3-enone into 4,7-dioxooctanoic acid in consistent yields of 50% with concomitant formation of 15% polymer. The corresponding ring opening of 1-(2-furyl)-5-methylhex-1-en-3-one proceeds in homogeneous acid solution in very high yield without polymer formation. The two furylalkenones can be reduced electrochemically to the corresponding furylalkylketones in good yields at a lead cathode in the presence of sodium hydrogen carbonate.