Synthesis of Dialkyl-Hydroxymethylphosphonates in Heterogeneous Conditions

Abstract

This article describes the synthesis of a series of dialkyl-hydroxymethylphosphonates bearing various alkyl ester groups by the Pudovik reaction. The employed method uses anhydrous potassium carbonate as a catalyst in heterogeneous (solid/liquid) or mixed (solid/liquid and homogenous) conditions. All these syntheses are performed without any phase transfer agent and involve an anionic intermediate in a low polar or apolar solvent. These different products, obtained with high yields, have been characterised by 1 H and 31 P NMR and also by mass spectrometry. A study of fragmentation in the FAB ionisation process is given.