Stobbe condensation

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.

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:[3] 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.