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]

See also

• Bouveault aldehyde synthesis

References

1. 1 2 G. Bryant Bachman (1943). "n-Hexaldehyde". Org. Synth. ; Coll. Vol., 2, p. 323 

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