Bodroux–Chichibabin aldehyde synthesis explained

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:

See also

• Bouveault aldehyde synthesis

References

• Bodroux, F. . . 1904 . 138 . 92 . Synthése d'aldehydes aromatiques . French . Synthesis of aromatic aldehydes .
• . 1904 . 37 . 186–188 . 10.1002/cber.19040370133 . Eine neue allgemeine Darstellungsmethode der Aldehyde . German . Tschitschibabin, A. E..
• Chemische Berichte . 1904 . 37 . 850–853 . 10.1002/cber.190403701140 . Ueber den Hexahydro-m-toluylaldehyd . German . Tschitschibabin, A. E..
• Smith, L. I. . Bayliss, M. . The Bodroux-Tschitschibabin, and the Bouveault Aldehyde Syntheses . . 1941 . 6 . 437 . 10.1021/jo01203a009 . 3.
• Smith, L. I. . Nichols, J. . The Synthesis of Aldehydes from Grignard Reagents. II. Polymethylbenzaldehydes . J. Org. Chem. . 1941 . 6 . 489 . 10.1021/jo01204a003 . 4.