Chemistry:Bodroux–Chichibabin aldehyde synthesis
From HandWiki
The Bodroux–Chichibabin aldehyde synthesis is a chemical reaction whereby a Grignard reagent is converted to an aldehyde one carbon longer.
Reaction of a Grignard reagent with triethyl orthoformate gives an acetal, which can be hydrolyzed to an aldehyde. For example, the synthesis of n-hexanal:[1]
Bodroux-Chichibabin hexanal[1]
See also
References
- ↑ 1.0 1.1 G. Bryant Bachman (1943). "n-Hexaldehyde". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=CV2P0323.; Collective Volume, 2, pp. 323
- Bodroux, F. (1904). "Synthése d'aldehydes aromatiques" (in French). Compt. Rend. 138: 92. http://gallica.bnf.fr/ark:/12148/bpt6k3092p/f98.image.r=Bodroux.
- Tschitschibabin, A. E. (1904). "Eine neue allgemeine Darstellungsmethode der Aldehyde" (in German). Chemische Berichte 37: 186–188. doi:10.1002/cber.19040370133. https://zenodo.org/record/1426098.
- Tschitschibabin, A. E. (1904). "Ueber den Hexahydro-m-toluylaldehyd" (in German). Chemische Berichte 37: 850–853. doi:10.1002/cber.190403701140. https://zenodo.org/record/1426092.
- Smith, L. I.; Bayliss, M. (1941). "The Bodroux-Tschitschibabin, and the Bouveault Aldehyde Syntheses". J. Org. Chem. 6 (3): 437. doi:10.1021/jo01203a009.
- Smith, L. I.; Nichols, J. (1941). "The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes". J. Org. Chem. 6 (4): 489. doi:10.1021/jo01204a003.
 |  |
