Bouveault-Blanc reduction

From Wikipedia, the free encyclopedia

The Bouveault-Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal.^[1][2][3]

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

[edit] 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.

[edit] References

1. ↑  Bouveault, L.; Blanc, G. Compt. Rend. 1903, 136, 1676.
2. ↑  Bouveault, L.; Blanc, G. Bull. Soc. Chim. France 1904, 31, 666.
3. ↑  Adkins, H.; Gillespie, R. H. Org. Syn., Coll. Vol. 3, p.671 (1955); Vol. 29, p.80 (1949). (Article)

[edit] See also

• Acyloin condensation