Synthesis of 4-Nonanolide and 4-Undecanolide from Nitroalkane

Abstract

4-Nonanolide (γ-nonalactone) and 4-undecanolide (γ-undecalactone), famous perfumes known as so-called Aldehyde C-18 and C-14, have been synthesized via lactonization of 4-hydroxy acid derived from 1-nitroalkane through the Michael addition to ethyl acrylate followed by the Nef reaction and reduction. Each step of the reaction sequence was found to proceed in fairly good yield, and thus this sequence prescribes a facile general synthetic method of γ-alkyl-γ-butyrolactone.