Abstract
A simple and mild procedure for the facile oxidation of alcohols to ketones and acids using a catalytic quantity of molecular iodine in combination with (diacetoxyiodo)benzene in acetonitrile is described. Direct oxidative methyl esterification of alcohols is also reported in methanol as solvent. Oxidation of alcohols is induced by iodonium ion generated in situ by the chemical oxidation of molecular iodine with (diacetoxyiodo)benzene.
Key words
alcohols - hypervalent elements - iodine - oxidation
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Experimental Procedure.
To a magnetically stirred solution of alcohol (1 mmol), iodine (0.1 mmol) in MeCN (15 mL) was added(diacetoxyiodo)benzene (1.1 mmol). The resulting red brown solution was stirred in an open vessel for the time as mentioned in Table
[1 2 S2 O3 and extracted with CH2 Cl2 (2 × 10 mL). The organic extract was dried over anhyd Na2 SO4 . Removal of the solvent and subsequent silica gel chromatography (petroleum ether and EtOAc) afforded the corresponding carbonyl compounds in the pure form.
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