Carboxylic Acids from Primary Alcohols and Aldehydes by a Pyridinium Chlorochromate Catalyzed Oxidation
Mo Hunsen*
*Department of Chemistry, Kenyon College, Gambier, OH 43022, USA, Email:
hunsenmkenyon.edu
M. Hunsen, Synthesis, 2005, 2487-2490.
DOI: 10.1055/s-2005-872085
Abstract
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.
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Details
The document describes a method for the oxidation of primary alcohols and aldehydes to carboxylic acids using pyridinium chlorochromate (PCC) as a catalyst and periodic acid (H5IO6) as the co-oxidant. This method is efficient, environmentally friendly, and provides quantitative yields. The oxidation of primary alcohols requires 2.2 equivalents of H5IO6, while aldehydes need 1.1 equivalents. The process works well for various substrates, including benzylic, aliphatic, and homobenzylic alcohols, and does not produce complex mixtures or require water addition, unlike CrO3-catalyzed oxidations. The method also successfully oxidizes electron-rich and electron-poor benzyl alcohols and aldehydes. Using water as a solvent with a phase transfer catalyst, the reaction is slower but simplifies the workup process. This PCC-catalyzed oxidation is notable for its efficiency, short reaction times, and high yields, making it a valuable method for synthesizing carboxylic acids in organic chemistry. Further research is ongoing to explore catalytic oxidations in aqueous phases.
Key Words
alcohols, aldehydes, oxidation, carboxylic acids, catalysis, pyridinium chlorochromate (PCC), periodic acid
ID: J66-Y2005-1640