Sodium metal is a one-electron reducing agent. Four equivalents of sodium are required to fully reduce each ester, although two more equivalents are typically consumed in deprotonating the product alcohols to alkoxides. Ethanol serves as a proton source.[1] The reaction produces sodium alkoxides, according to the following stoichiometry:
In practice, considerable sodium is consumed by the formation of hydrogen.[citation needed] For this reason, an excess of sodium is often required. Because the hydrolysis of sodium is rapid, not to mention dangerous, the Bouveault-Blanc reaction requires anhydrous ethanol and can give low yields with insufficiently dry ethanol.[9][8] The mechanism of the reaction follows:[1]
Consistent with this mechanism, sodium-ethanol mixtures will also reduce ketones to alcohols.[10]
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.[11] Another modification uses a sodium dispersion.[12][13]
^Bouveault, L.; Blanc, G. (1903).『Préparation des alcools primaires au moyen des acides correspondants』[Preparation of primary alcohols by means of the corresponding acids]. Compt. Rend. (in French). 137: 60–62.
^Reid, E. E.; Cockerille, F. O.; Meyer, J. D.; Cox, W. M.; Ruhoff, J. R. (1935). "Oleyl Alcohol". Organic Syntheses. 15: 51. doi:10.15227/orgsyn.015.0051.
^Whitmore, Frank C.; Otterbacher, T. (1930). "2-Heptanol". Organic Syntheses. 10: 60. doi:10.15227/orgsyn.010.0060.
^Bodnar, Brian S.; Vogt, Paul F. (2009). "An Improved Bouveault-Blanc Ester Reduction with Stabilized Alkali Metals". J. Org. Chem.74 (6): 2598–2600. doi:10.1021/jo802778z. PMID19219971.
