The Bouveault–Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal. It was first reported by Louis Bouveault and Gustave Louis Blanc in 1903. Bouveault and Blanc demonstrated the reduction of ethyl oleate and n-butyl oleate to oleyl alcohol. Refined versions of the conversion have been reported.
:350px|The Bouveault-Blanc reduction
This reaction is used commercially although for laboratory scale reactions it was made obsolete by the introduction of lithium aluminium hydride.
This approach to reducing esters was widely used prior to the availability of hydride reducing agents such as lithium aluminium hydride and related reagents. It requires vigorous reaction conditions and has a significant risk of fires, explaining its relative unpopularity. One modification involves encapsulating the alkali metal into a silica gel, which has a safety and yield profile similar to that of hydride reagents. Another modification uses a sodium dispersion.
See also
- Acyloin condensation – The reductive coupling of esters, using sodium, to yield an α-hydroxyketone
- Akabori amino-acid reaction – The reduction of amino acid esters, by sodium, to yield aldehydes
- Birch reduction – For the reduction of alkenes using sodium
- Bouveault aldehyde synthesis – Another organometallic reaction by Bouveault where a Grignard reagent is converted to an aldehyde
Additional historic references
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