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Organic-Solvent-Free Phase-Transfer Oxidation of Alcohols Using Hydrogen Peroxide

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Martin Hulce and David W. Marks

Department of Chemistry, Creighton University, Omaha, NE 68178-0104

J. Chem. Educ., 2001, 78 (1), p 66

DOI: 10.1021/ed078p66

Publication Date (Web): January 1, 2001

Section:

History, Education, and Documentation

Abstract

Organic-solvent-free oxidations of alcohols using aqueous hydrogen peroxide in the presence of sodium tungstate and phase-transfer catalysts provide a general, safe, simple, and cost-effective means to prepare ketones. Six representative alcohols, 1-phenylethanol, 1-phenylpropanol, benzhydrol, 4-methylbenzhydrol, cis,trans-4-tert-butylcyclohexanol, and benzyl alcohol are oxidized to the corresponding aldehyde or ketone over 1-3 hours in 81-99% yields. Purities are very high, with only small to trace amounts of starting alcohol remaining. Experiments can be readily designed for one or two 3-hour laboratory periods, integrating the various techniques of extraction, drying, filtration, column chromatography, gas chromatography, NMR and IR spectroscopy, and reaction kinetics.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Catalysis

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