Abstract
A chemoselective and effective procedure for the conversion of benzylic and allylic alcohols into the corresponding carbonyl compounds using sodium nitrate-3-methylimidazolinium hydrogensulfate is reported.
Key words
Brønsted acidic ionic liquids - oxidation - alcohols - aldehydes - ketones
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21 Preparation of [Hmim]+ HSO4
- : 1-methylimidazole (0.82 g, 0.01 mol) was placed in a two-necked flask with stirrer and was cooled to 0 °C. MeCN (10 mL) was added and then H2 SO4 (0.98 g, 0.01 mol) was added slowly with stirring. The mixture was stirred for 30 min and the MeCN was removed by simple decanting.
22 General procedure: In a mortar a mixture of benzylic alcohol (1.0 mmol), sodium nitrate (0.085 g, 1.0 mmol), and [Hmim]+ HSO4
- (0.25 mmol) was ground with a pestle. The reaction times and temperatures are shown in Table
[1 2 O and washed with H2 O. The organic layer was dried over Na2 SO4 and evaporated under reduced pressure. Purification of the residue using flash column chromatography (silica gel, EtOAc-cyclohexane, 20:80) provided the pure carbonyl compounds.
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2007, accepted for publication
