Bouveault aldehyde synthesis: Difference between revisions
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The '''Bouveault aldehyde synthesis''' is a one-pot [[chemical reaction]] that converts a primary [[alkyl halide]] to an [[aldehyde]] one carbon longer.<ref>{{cite journal | author = Bouveault, L. | journal = [[Bull. Soc. Chim. | The '''Bouveault aldehyde synthesis''' is a one-pot [[chemical reaction]] that converts a primary [[alkyl halide]] to an [[aldehyde]] one carbon longer.<ref>{{cite journal | author = Bouveault, L. | journal = [[Bull. Soc. Chim. Fr.]] | year = 1904 | volume = 31 | pages = 1306}}</ref><ref>{{cite journal | author = Bouveault, L. | journal = [[Bull. Soc. Chim. Fr.]] | year = 1904 | volume = 31 | pages = 1322}}</ref> | ||
:[[Image:Bouveault_Aldehyde_Synthesis_Scheme.png|500px|The Bouveault aldehyde synthesis]] | :[[Image:Bouveault_Aldehyde_Synthesis_Scheme.png|500px|The Bouveault aldehyde synthesis]] | ||
Revision as of 18:12, 23 February 2009
The Bouveault aldehyde synthesis is a one-pot chemical reaction that converts a primary alkyl halide to an aldehyde one carbon longer.[1][2]
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
- ↑ Bouveault, L. (1904). Bull. Soc. Chim. Fr. 31: 1306.
- ↑ Bouveault, L. (1904). Bull. Soc. Chim. Fr. 31: 1322.
- Smith, L. I.; Nichols, J. (1941). "The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes". J. Org. Chem. 6: 489. doi:.
- Sice, Jean (1953). "Preparation and Reactions of 2-Methoxythiophene". J. Am. Chem. Soc. 75: 3697. doi:.
- Jones, E. R. H. (1958). "210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons". J. Chem. Soc.: 1054. doi:.