Potassium Hydroxide → 4-(Benzyloxy)-3,5-dimethylphenol

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A solution of 18.0 g (75 mmol) of 3,5-dimethyl-4-(phenylmethoxy)benzaldehyde (Example F) and 17.1 g of 85% meta-chloroperbenzoic acid (14.5 g contained; 1.2×75 mmol) in 600 mL of dichloromethane is stirred at reflux for 16 hours. The cooled solution is stirred with 2×150 mL saturated sodium bicarbonate solution, 150 mL of 10% sodium bisulfite solution, then dried (magnesium sulfate) and evaporated leaving 15.2 g of a turbid oil. A solution of the latter in 225 mL of methanol is stirred at ambient temperature with a solution of 12.6 g (3×75 mmol) of potassium hydroxide in 75 mL of water. After 18 hours the methanol is removed on a rotary evaporator and the residual aqueous solution is diluted with 200 mL of water, and back-extracted with 150 mL of diethyl ether. The aqueous solution is acidified with 50 mL of 6N hydrochloric acid solution and the product is isolated with diethyl ether. The diethyl ether solution is washed with brine, dried (magnesium sulfate) and evaporated leaving 8.1 g of a brown solid. The original diethyl ether extract is dried (magnesium sulfate) and evaporated leaving 10.7 g of a light yellow viscous oil. The two fractions are combined and the crude precipitate is chromatographed on a 4.5 cm column containing 250 g of silica gel prepared in toluene. Elution with 98% toluene:2% ethyl acetate affords 16.6 g of the product. Recrystallization from cyclohexane affords the title compound as off-white leaflets; mp 89°-91° C.

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