Pinacol Coupling Reaction
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.
Mechanism of the Bouveault-Blanc Reduction
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.
Evaluating a Sodium Dispersion Reagent for the Bouveault-Blanc Reduction of Esters
J. An, D. N. Work, C. Kenyon, D. J. Procter, J. Org. Chem., 2014, 79, 6743-6747.
Development of a Modified Bouveault-Blanc Reduction for the Selective Synthesis of α,α-Dideuterio Alcohols
M. Han, X. Ma, S. Yao, Y. Ding, Z. Yan, A. Adijiang, Y. Wu, H. Li, Y. Zhang, P. Lei, Y. Ling, J. An, J. Org. Chem., 2017, 82, 1285-1291.
Sodium in silica gel (Na-SG) - a safe, free-flowing powder - has been used for the Bouveault-Blanc reduction of various aliphatic esters. Primary alcohols were prepared in excellent yield under mild reaction conditions.
B. S. Bodnar, P. F. Vogt, J. Org. Chem., 2009, 74, 2598-2600.