Ethyl Acetate → 1-[4-(1-Hydroxyethyl)phenyl]ethan-1-one

참여 물질

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To a solution of 1-(4-acetylphenyl)-ethanone (1.0 g, 6.2 mmol) in dry methanol (30 mL) at 0° C. was slowly added NaBH4 (0.07 g, 1.9 mmol). The reaction mixture was allowed to stir at 0° C. for 4 h, at which time silica gel TLC in hexanes and ethyl acetate (1:1 v/v, rf=0.5 desired product) showed a mixture of starting material, desired product, and the double-reduction side product. The reaction mixture was treated slowly with 1 N HCl solution (1 mL) at 0° C. until bubbling was no longer observed. Methanol was removed in vacuo to provide an orange residue, which was then partitioned between ethyl acetate (100 mL) and 1 N HCl (100 mL). The organic layer was washed with the 1 N HCl followed by a saturated NaCl solution (100 mL), dried over MgSO4, filtered and concentrated in vacuo to afford an orange oil. The crude product was purified by flash chromatography through a silica gel column with hexanes and ethyl acetate (65:35 v/v) to provide the desired compound (0.55 g, 54%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.97 (d, 2H), 7.50 (d, 2H), 5.00 (dt, 1H), 2.61 (s, 3H), 1.52 (d, 3H).

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