Aldehydes undergo the Aldol reaction to form β-hydroxyaldehydes.
Esters on the otherhand undergo Claisen condensation to form β-ketoesters.
In the Claisen condensation, an ester enolate forms in equilibrium with the ester. Alkoxide bases are commonly used to avoid any hydrolysis that may occur if OH- were used. The ester enolate undergoes acyl substitution with an ester that has not been deprotonated.
Similar to the Aldol reaction Crossed Claisen's are possible giving four β-ketoesters products.
Crossed Claisen are more efficient when directed (i.e. one of the esters cannot form an enolate...no α-protons). You can also play the slow addition game as in the Aldol condensation to maximize efficiency/yield.
With diesters you can also do intramolecular Claisen Condensation (Dieckman Cyclization).
Login