Tishchenko Reaction

The Tishchenko Reaction is a disproportionation reaction that allows the preparation of esters from two equivalents of an aldehyde.

Mechanism of the Tishchenko Reaction

The aluminium alkoxide acts as a Lewis acid to coordinate with one molecule of the aldehyde, and to facilitate the addition of a second equivalent of aldehyde, generating a hemiacetal intermediate:

This species undergoes an intramolecular 1,3-hydride shift that results in the production of the aluminium-coordinated ester.

A potential side reaction is the involvement of one of the alkoxide groups from the catalyst:

This can be minimised, if the reaction is conducted at low temperatures and low catalyst loadings.