Dichloromethane → 3-[4-(4-Acetyl-3-hydroxy-2-methyl-phenoxymethyl)-benzyl]-benzoic acid

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Reaction Steps

A solution of 3-{[4-(4-acetyl-3-hydroxy-2-methyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzoic acid (80 mg, 0.197 mmol), triethylsilane (250 μL, 1.57 mmol), boron trifluoride diethyl etherate (70 μL, 0.542 mmol), and dichloromethane (2 mL) is stirred 1 hr at room temperature. The mixture is diluted with water and extracted with ethyl acetate (2×10 mL). The combined extracts are dried over magnesium sulfate, filtered and concentrated. The residue is recrystallized from dichloromethane/hexanes to give (54 mg, 70%) the title compound, as a white solid. 1H NMR (DMSO-d6) δ 12.92 (bs, 1H), 12.85 (s, 1H), 7.78-7.82 (m, 3H), 7.27-7.49 (m, 6H), 6.72 (d, 1H), 5.23 (s, 2H), 4.06 (s, 2H), 2.52 (s, 3H), 2.04 (s, 3H). LCMS M−1 389.

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