Bouveault‐Blanc Reduction

Abstract

Abstract The reduction of esters into alcohols with sodium in ethanol, in which sodium serves as a single electron reducing agent and ethanol is the proton donor, is generally known as the Bouveault–Blanc reduction. Other alcohols have also been applied as proton donors. In the absence of proton donor, the reduction of esters with sodium leads to the formation of acyloins. It has also been pointed out that the Bouveault–Blanc reduction under appropriate conditions effects the ring reduction of aromatic compounds. This reaction is an inexpensive substitute for lithium aluminum hydride reductions of esters in industrial production before the development of the metal hydride. It has been proved in the present study that the ketyl radical can cyclize to form cyclic or spirocyclic molecules if a double bond exists in the appropriate location of the ester.