Bouveault-Blanc reduction


Bouveault-Blanc reduction

The Bouveault-Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal.Ref|Bouveault1903Ref|Bouveault1904Ref|Adkins1949

This reaction is an inexpensive and large-scale alternative to lithium aluminium hydride reduction of esters.

Reaction mechanism

Sodium metal is a single-electron reducing agent, meaning the sodium metal will transfer electrons one at a time. Four sodium atoms are required to fully reduce each ester to alcohols. Ethanol serves as a proton source.

References

# Bouveault, L.; Blanc, G. "Compt. Rend." 1903, "136", 1676.
# Bouveault, L.; Blanc, G. "Bull. Soc. Chim. France" 1904, "31", 666.
# Adkins, H.; Gillespie, R. H. "Org. Syn.", Coll. Vol. 3, p.671 (1955); Vol. 29, p.80 (1949). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0671 Article] )

ee also

*Acyloin condensation


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