Bodroux–Chichibabin aldehyde synthesis

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]

References

^ ^a ^b G. Bryant Bachman (1943). "n-Hexaldehyde". Organic Syntheses ; Collected Volumes, vol. 2, p. 323.

Bodroux, F. (1904). "Synthése d'aldehydes aromatiques" [Synthesis of aromatic aldehydes]. Compt. Rend. (in French). 138: 92.
Tschitschibabin, A. E. (1904). "Eine neue allgemeine Darstellungsmethode der Aldehyde". Chemische Berichte (in German). 37: 186–188. doi:10.1002/cber.19040370133.
Tschitschibabin, A. E. (1904). "Ueber den Hexahydro-m-toluylaldehyd". Chemische Berichte (in German). 37: 850–853. doi:10.1002/cber.190403701140.
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.