Illustrated Glossary of Organic Chemistry

Malonic ester synthesis: A convenient method for synthesis of a carboxylic acid bearing an alkyl group on the α-carbon. The method is particularly useful to avoid over-alkylation. The process is illustrated with the synthesis of 3-phenylpropanoic acid, shown below. Compare with the acetoacetic ester synthesis, used to synthesize a ketone bearing an alkyl group on the α-carbon.

Diethyl malonate	Form enolate		SN2 alkylation
	Ester hydrolysis		Decarboxylation
	Tautomerization	3-Phenylpropanoic acid