Water → 1-[4-(Methoxymethoxy)phenyl]-2-phenylbutan-1-one

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To a stirred solution of 13 (99.0 g, 0.46 mol) in anhydrous THF (750 mL) was added n-BuLi (1.6 M in hexanes, 310 mL, 0.50 mol) dropwise at −78° C. The reaction mixture was stirred for 30 min and 14 (90.1 g, 0.43 mol) dissolved in THF (500 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h and then slowly warmed to 0° C. H2O (500 mL) was added and the volatiles were removed under reduced pressure. The residue was extracted with Et2O (3×500 mL) and the combined extracts were washed with water (500 mL) and brine (500 mL). The mixture was dried over MgSO4 and concentrated. The residue was recrystallized from hexanes to afford 97.6 g (80%) of 15 as white needles. 1HNMR (400 MHz, DMSO-d6): δ 0.79 (t, J=7.3 Hz, 3H), 1.68 (h, J=7.0 Hz, 1H), 2.03 (h, J=7.0 Hz, 1H), 3.32 (s, 3H), 4.65 (t, J=7.3 Hz, 1H), 5.21 (s, 2H), 7.03 (d, J=8.8 Hz, 2H), 7.15 (t, J=7.1 Hz, 1H), 7.23-7.30 (m, 4H), 7.98 (d, J=8.8 Hz, 2H).

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