Formose reactions. Part 3. Selective formose reaction catalyzed by organic bases

Abstract

In the formose reaction catalyzed by an organic base such as diethylaminoethanol, a compound with a potential 1,2-oxy-oxo-structure, an acceleration effect was observed on the main reaction and a suppression effect on the Cannizzaro side-reaction. Organic bases with high basicity not only showed high catalytic activity but also enabled a selective formose reaction to occur, giving 2-C-(hydroxymethyl)glycerol as the main product. A mechanism to account for the formation of 2-C-(hydroxymethyl)glycerol is proposed.