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Jain, Sharma, and Sain
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Chem. Res. 1997, 30, 169.
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V.B.; Jain, S.L.; Sain, B. Tetrahedron Lett. 2003, 44, 383; (c) Jain,
S.L.; Sain, B. J. Mol. Catal. 2001, 176, 102; (d) Rao, T.V.; Sain, B.;
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12. 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 fol-
lowed 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 elu-
ent, evaporation of the solvent gave benzoic acid (234 mg, 96%).
Other a-hydroxycarbonyl compounds were oxidized using this pro-
cedure 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 a-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 a-dicarbonyl compounds (benzil and anisil) were oxidized
to their corresponding acids.