Malonic Ester Synthesis

Malonic Esters Are More Acidic Than Simple Esters, So That Alkylations Can Be Carried Out Via Enolate Formation Promoted By Relatively Mild Bases Such As Sodium Alkoxide, And Subsequent Alkylation With Halides. An Excess Of Ester Must Be Used To Prevent Dialkylated Products. Carboxylic Acids May Optionally Be Obtained After Hydrolysis And Decarboxylation.

Intramolecular Dialkylation Can Lead To Interesting Products Such As Cyclobutanes: