Categories: C=O Bond Formation > Synthesis of carboxylic acids >
Synthesis of carboxylic acids by oxidation of alcohols
Name Reactions
Recent Literature
A CrO3-catalyzed oxidation of primary alcohols to carboxylic acids
proceeds smoothly with only 1-2 mol % of CrO3 and 2.5 equivalents of
H5IO6 in wet MeCN to give the carboxylic acids in
excellent yield. No significant racemization is observed for alcohols with
adjacent chiral centers. Secondary alcohols are cleanly oxidized to ketones.
M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, P. J.
Reider, Tetrahedron Lett., 1998,
39, 5323-5326.
Catalytic use of o-iodoxybenzoic acid (IBX) in the presence of Oxone as a
co-oxidant is demonstrated for the oxidation of primary and secondary alcohols.
In addition, the in situ oxidation
of 2-iodosobenzoic acid (IBA) and even commercially available 2-iodobenzoic acid
(2IBAcid) by Oxone to IBX allows the use of these less hazardous reagents, in
place of potentially explosive IBX, as catalytic oxidants.
A. P. Thottumkara, M. S. Bowsher, T. K. Vinod, Org. Lett., 2005, 7, 2933-2936.
A facile and quantitative preparation of carboxylic acids by a pyridinium
chlorochromate (PCC) catalyzed (2 mol%) oxidation of primary alcohols and
aldehydes using 2.2 equivalents and 1.1 equivalents of H5IO6, respectively, in
acetonitrile is described here.
M. Hunsen, Synthesis, 2005, 2487-2490.
