:Bouveault aldehyde synthesis
{{Reactionbox
| Name = Bouveault aldehyde synthesis
| Type = Carbon-carbon bond forming reaction
| NamedAfter = Louis Bouveault
| Section3 = {{Reactionbox Identifiers
| RSC_ontology_id = 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.{{cite journal | author = Louis Bouveault | journal = Bull. Soc. Chim. Fr. | year = 1904 | volume = 31 | pages = 1306–1322 | title = Modes de formation et de préparation des aldéhydes saturées de la série grasse | language = French | trans-title = Methods of preparation of saturated aldehydes of the aliphatic series}}{{cite journal | author = Louis Bouveault | journal = Bull. Soc. Chim. Fr. | year = 1904 | volume = 31 | pages = 1322–1327 | title = Nouvelle méthode générale synthétique de préparation des aldéhydes | trans-title = Novel general synthetic method for preparing aldehydes | language = French}}
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.Jie Jack Li. Name Reactions: A Collection of Detailed Reaction Mechanisms. Springer, 2003. {{ISBN|3-540-40203-9}}
See also
References
- {{cite journal |author1=Smith, L. I. |author2=Nichols, J. | title = The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes | journal = J. Org. Chem. | year = 1941 | volume = 6 | pages = 489 | doi = 10.1021/jo01204a003 | issue = 4}}
- {{cite journal | journal = J. Am. Chem. Soc. | year = 1953 | volume = 75 | pages = 3697–3700 | doi = 10.1021/ja01111a027 | author = Sice, Jean | title = Preparation and Reactions of 2-Methoxythiophene | issue = 15}}
- {{cite journal | journal = J. Chem. Soc. | year = 1958 | pages = 1054–1059 | doi = 10.1039/jr9580001054 | title = 210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons | author = Jones, E. R. H.}}
{{Organic reactions}}
Category:Carbon-carbon bond forming reactions