Studies on Phenolic Lactones

Part III. Synthesis of (±) Hibalactone

Abstract

(±) Hibalactone, α-piperonylidene-β-piperonyl-butyrolactone, was synthesized by the following method. α-piperonylidene-β-piperonyl-succinic acid dimethylester was reduced with lithium aluminum hydride to 2-piperonylidene-3-piperonyl-1, 4-butanediol, m. p. 117°C. Oxidation of the glycol with manganese dioxide in acetone yielded α-piperonylidene-β-piperonyl-_ϒ-hydroxy-butyraldehyde, which afforded racemic hibalactone, m. p. 154_??_5°, after oxidation with silver oxide and lactonization.