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.^[1]

Additional recommended knowledge

Guide to balance cleaning: 8 simple steps

Daily Sensitivity Test

What is the Correct Way to Check Repeatability in Balances?

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. ^  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