Hydrogen Peroxide → 2-(4-Benzyloxy-phenyl)-3-ethyl-5-hydroxymethyl-4-methyl-cyclohexanol

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To the solution of [4-(4-benzyloxy-phenyl)-5-ethyl-6-methyl-cyclohex-3-enyl]-methanol (3.1 g, 6.8 mmol) in THF (50 mL) was added BH3.S(CH3)2 solution (1.0 M in THF, 10.3 mL, 1.5 eq.) at 0° C. The reaction mixture was refluxed for 4 h and then cooled to 0° C. NaOH (20% aqueous, 30 mL) and H2O2 (50% in H2O, 21 mL) were added at 0° C. The reaction mixture was then stirred at 0˜25° C. for 4 h. The reaction mixture was then diluted with ethyl acetate/H2O (400 mL/200 mL). The organic layer was separated, dried over MgSO4 and purified on SiO2 (50˜100% ethyl acetate/hexane) to yield 2-(4-benzyloxy-phenyl)-3-ethyl-5-hydroxymethyl-4-methyl-cyclohexanol.

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