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General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids

Lauren R. Cafiero and Timothy S. Snowden*

*Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 35487-0336, Email:

L. R. Cafiero, T. S. Snowden, Org. Lett., 2008, 10, 3853-3856.

DOI: 10.1021/ol8016484 (free Supporting Information)


The reaction of aldehydes with trichloromethide followed by reductive ring opening under basic conditions affords homologated carboxylic acids in high yields. This operationally simple procedure provides a practical, efficient alternative to other homologation protocols and is compatible with sensitive aldehydes including enals and enolizable substrates.

see article for more examples

proposed reaction pathway

Preparation of One-Carbon Homologated Amides from Aldehydes or Primary Alcohols

M. K. Gupta, Z. Li, T. S. Snowden, Org. Lett., 2014, 16, 1602-1605.

Practical Approach to α- or γ-Heterosubstituted Enoic Acids

J. L. Shamshina, T. S. Snowden, Org. Lett., 2006, 8, 5881-5884.

Key Words

Jocic Reaction, Trichloromethyl Carbinols, Carboxylic Acids, Sodium Borohydride

ID: J54-Y2008-2440