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A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

Mangzhu Zhao*, Jing Li, Zhiguo Song, Richard Desmond, David M. Tschaen, Edward J. J. Grabowski and Paul J. Reider

*Process Research Department, Merck Research Laboratories, Merck & Co. Inc., P.O. Box 2000, Rahway, NJ 07065, USA

M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, P. J. Reider, Tetrahedron Lett., 1998, 39, 5323-5326.

DOI: 10.1016/S0040-4039(98)00987-3


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.

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Key Words

Jones oxidation, oxidation of alcohols, chromium trioxide, periodic acid

ID: J72-Y1998-600