Bouveault aldehyde synthesis

The Bouveault aldehyde synthesis is a one-pot chemical reaction that converts a primary alkyl halide to an aldehyde one carbon longer.Template:Ref

The Bouveault aldehyde synthesis

Reaction mechanism

The first step of the Bouveault aldehyde synthesis is the formation of the Grignard reagent. Upon addition of a N,N-disubstituted formamide (such as DMF) a hemiaminal is formed, which can easily be hydrolyzed into the desired aldehyde.

References

1. Template:Note Bouveault, L. Bull. Soc. Chim. France 1904, 31, 1306 & 1322.
2. Smith, L. I.; Nichols, J. J. Org. Chem. 1941, 6, 489.
3. Sicé, J. J. Am. Chem. Soc. 1953, 75, 3697.
4. Jones, E. R. H. et al. J. Chem. Soc. 1958, 1054.

See also

• Bodroux-Chichibabin aldehyde synthesis
• Duff reaction