Bouveault aldehyde synthesis

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Bouveault aldehyde synthesis
Named after Louis Bouveault
Reaction type Carbon-carbon bond forming reaction
Identifiers
RSC ontology ID RXNO:0000533

The Bouveault aldehyde synthesis (also known as the Bouveault reaction) is a one-pot substitution reaction that replaces an alkyl or aryl halide with a formyl group using a N,N-disubstituted formamide.[1][2] For primary alkyl halides this produces the homologous aldehyde one carbon longer. For aryl halides this produces the corresponding carbaldehyde. Bouveault aldehyde synthesis is an example of a formylation reaction.

The Bouveault aldehyde synthesis

Reaction mechanism[edit]

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 .

Variations[edit]

Variants using organolithium reagents instead of magnesium-based Grignard reagents are also considered Bouveault aldehyde syntheses.[3]

See also[edit]

References[edit]

  1. ^ Bouveault, L. (1904). "Modes de formation et de préparation des aldéhydes saturées de la série grasse" [Methods of preparation of saturated aldehydes of the aliphatic series]. Bull. Soc. Chim. Fr. 31: 1306–1322. 
  2. ^ Bouveault, L. (1904). "Nouvelle méthode générale synthétique de préparation des aldéhydes" [Novel general synthetic method for preparing aldehydes]. Bull. Soc. Chim. Fr. 31: 1322–1327. 
  3. ^ Jie Jack Li. Name Reactions: A Collection of Detailed Reaction Mechanisms. Springer, 2003. ISBN 3-540-40203-9