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.

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.

See also

• Bodroux-Chichibabin aldehyde synthesis
• Duff reaction

References

• Smith, L. I.; Nichols, J. (1941). "The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes". J. Org. Chem. 6: 489. doi:10.1021/jo01204a003. 
• Sice, Jean (1953). "Preparation and Reactions of 2-Methoxythiophene". J. Am. Chem. Soc. 75: 3697. doi:10.1021/ja01111a027. 
• Jones, E. R. H. (1958). "210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons". J. Chem. Soc.: 1054. doi:10.1039/jr9580001054.