Bouveault aldehyde synthesis
Chemical reaction
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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. The Bouveault aldehyde synthesis is an example of a formylation reaction, and is named for French scientist Louis Bouveault.
| Bouveault aldehyde synthesis | |
|---|---|
| Named after | Louis Bouveault |
| Reaction type | Carbon-carbon bond forming reaction |
| Identifiers | |
| RSC ontology ID | RXNO:0000533 |
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 dimethylformamide) a hemiaminal is formed, which can easily be hydrolyzed into the desired aldehyde.
Variations
Variants using organolithium reagents instead of magnesium-based Grignard reagents are also considered Bouveault aldehyde syntheses.[3]