Hydrochloric Acid → (-)-Menthol

Beteiligte Stoffe

Reaktionsschritte

A solution of 4-phenylbutan-2-ol (100.1 mg, 0.666 mmol), Nor-AZADO (0.92 mg, 6.66 μmol), potassium bromide (39.7 mg, 0.333 mmol) and hydrochloric acid (11.1 μl, 0.133 mmol) in dichloromethane (0.67 ml) was added with 30% aqueous hydrogen peroxide (102.1 μl, 1.000 mmol), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added with saturated aqueous sodium carbonate (2 ml) and saturated aqueous sodium thiosulfate (2 ml), and the mixture was stirred at room temperature for 2 hours, and then extracted with dichloromethane. The organic layer was dried over sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the objective compound (95.3 mg; yield, 96.5%). The spectrum data were found to be the same as those obtained in Example 5, (b).

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