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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 22
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Original Articles

Methyltrioxorhenium Catalyzed Oxidative Cleavage of α-Hydroxycarbonyl Compounds to Carboxylic Acids with Hydrogen Peroxide

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Pages 3875-3878 | Published online: 19 Aug 2006

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  • Typical experimental procedure: To a stirred solution of benzoin (212 mg, 1 mmol) in acetonitrile (5 mL) was added 30% aqueous hydrogen peroxide (1 mL solution) mixed with drying agent followed by the addition of methyltrioxorhenium (0.01 mmol, 1.0 mol%) and the reaction mixture was refluxed for the 6 h. At the end of reaction, the reaction mixture was treated with excess MnO2 (for destruction of H2O2) followed by filtration and passing through a short column of silica gel using dichloromethane as eluent, evaporation of the solvent gave benzoic acid (234 mg, 96%). Other α-hydroxycarbonyl compounds were oxidized using this procedure and their reaction times and yields are given in Table 1. The products were identified by comparing their physical and spectral data with those of authentic samples reported in literature. In case of asymmetric α-hydroxycarbonyl compounds the identity of the acids was established through GC by comparing the retention time of their methyl esters with those of authentic samples. Similarly α-dicarbonyl compounds (benzil and anisil) were oxidized to their corresponding acids

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