Claisen Condensation

Because esters can contain α hydrogens they can undergo a condensation reaction similar to the aldol reaction called a Claisen Condensation. In a fashion similar to the aldol, one ester acts as a nucleophile while a second ester acts as the electrophile. During the reaction a new carbon-carbon bond is formed. The product is a β-keto ester. A major difference with the aldol reaction is the fact that hydroxide cannot be used as a base because it could possibly react with the ester. Instead, an alkoxide version of the alcohol used to synthesize the ester is used to prevent transesterification side products.