Solvent and ion-pair effects on the self-condensation of linear aliphatic aldehydes: selective synthesis of substituted acrylaldehydes and glycol monoesters

Abstract

Self-condensation of linear aliphatic aldehydes (1) in the presence of magnesium phenolates as catalysts has been studied. These reactions are shown to be strongly dependent on the solvent, the reagent: catalyst ratio, and the cation and anion constituting the ion-pair. Conditions for selective synthesis of 1,3-diol monoesters (2) and (3) and 2,3-dialkylacrylaldehydes (4) are given. The reaction mechanism is discussed.