To a mixture of N-methylmorpholine-N-oxide.2H2O (18.2 g, 155 mmol), water (50 mL), acetone (20 mL), and osmium tetroxide (80 mg) in t-butanol (8 mL) was added distilled cyclohexene (10.1 mL, 100 mmol). The reaction was slightly exothermic initially and was maintained at room temperature with a water bath. The reaction was complete after stirring overnight at room temperature under nitrogen. A slurry of 1 g of sodium hydrosulfifite, 12 g of magnesium silicate (magnesol), and 80 ml of water was added, and the magnesol was fifiltered. The fifiltrate was neutralized to pH 7 with 1 N H2SO4, the acetone was evaporated under vacuum, and the pH was further adjusted to pH 2. The solution was saturated with NaCl and extracted with EtOAc. The aqueous phase was concentrated by azeotroping with n-butanol and further extracted with ethyl acetate. The combined ethyl acetate layers were dried and evaporated, yielding 11.2 g (96.6%) of crystalline solid. Recrystallization from ether provided 10.6 g (91%) of cis-1,2-cyclohexanediol, mp 95–97°C.
Reference: Van Rheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973−1976.
