Bouveault-Blanc Reduction

This method is an inexpensive substitute for LAH reductions of esters in industrial production, and was the only alternative prior to the development of the metal hydride reducing agents. This dissolving metal reduction is also related to the Birch Reduction.

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Mechanism

Sodium serves as single electron reducing agent and EtOH is the proton donor. If no proton donor is available, dimerization will take place, as the Acyloin Condensation.