Bouveault aldehyde synthesis

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.Ref|Bouveault1904

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

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

ee also

*Bodroux-Chichibabin aldehyde synthesis
*Duff reaction


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