Bouveault aldehyde synthesis: Difference between revisions
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The | The '''Bouveault aldehyde synthesis''' is a one-pot [[chemical reaction]] that converts a primary [[alkyl halide]] to an [[aldehyde]] one carbon longer.{{Ref|Bouveault1904}} | ||
[[Image:Bouveault_Aldehyde_Synthesis_Scheme.png|center|500px|The Bouveault aldehyde synthesis]] | [[Image:Bouveault_Aldehyde_Synthesis_Scheme.png|center|500px|The Bouveault aldehyde synthesis]] | ||
==Reaction mechanism== | ==Reaction mechanism== | ||
The first step of the | 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|DMF]]) a [[hemiaminal]] is formed, which can easily be [[hydrolyzed]] into the desired aldehyde. | ||
==References== | ==References== | ||
Revision as of 19:24, 29 October 2006
The Bouveault aldehyde synthesis is a one-pot chemical reaction that converts a primary alkyl halide to an aldehyde one carbon longer.Template:Ref
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
- Template:Note 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.