Bouveault aldehyde synthesis: Difference between revisions
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[[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 | ==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|DMF]]) a [[hemiaminal]] is formed, which can easily be [[hydrolyzed]] into the desired aldehyde. | 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. | ||
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==See also== | ==See also== | ||
[[Bodroux-Chichibabin aldehyde synthesis]] | *[[Bodroux-Chichibabin aldehyde synthesis]] | ||
{{reaction-stub}} | {{reaction-stub}} | ||
[[Category:Organic reactions]] | [[Category:Organic reactions]] | ||
Revision as of 22:48, 14 June 2005
The Bouveault aldehyde synthesis is a one-pot chemical reaction that converts a primary alkyl halide to an aldehyde one carbon longer.
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
- 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.