Bouveault aldehyde synthesis explained

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.

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]

See also

• Bodroux-Chichibabin aldehyde synthesis
• Bouveault–Blanc reduction
• Duff reaction

References

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

• Smith, L. I. . Nichols, J. . The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes . . 1941 . 6 . 489 . 10.1021/jo01204a003 . 4.
• . 1953 . 75 . 3697–3700 . 10.1021/ja01111a027 . Sice, Jean . Preparation and Reactions of 2-Methoxythiophene . 15.
• . 1958 . 1054–1059 . 10.1039/jr9580001054 . 210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons . Jones, E. R. H..