The Stobbe condensation entails the reaction of an aldehyde or ketone with an ester of succinic acid to generate alkylidene succinic acid or related derivatives.[1] The reaction consumes one equivalent of metal alkoxide. Commonly, diethylsuccinate is a component of the reaction. The usual product is salt of the half-ester. The Stobbe condensation is named after its discoverer, Hans Stobbe, whose work involved the sodium ethoxide-induced condensation of acetone and diethyl succinate.[2]
An example is the reaction of benzophenone with diethyl succinate:
A reaction mechanism that explains the formation of both an ester group and a carboxylic acid group is centered on a lactone intermediate (5):
The Stobbe condensation is also illustrated by the synthesis of the drug tametraline.[3]