m-Chloroperbenzoic acid → 3-(2-Methoxyphenyl)-4,5-methylenedioxyphenol

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Reaction Steps

A solution of 3-(2-methoxyphenyl)-4,5-methylenedioxybenzaldehyde (0.850 g, 3.32 mmol), m-chloroperbenzoic acid (1.431 g, 8.29 mmol) in CH2Cl2 (25 mL) was heated to reflux overnight. The resulting orange mixture was evaporated, dissolved into MeOH (15 mL) and 2.5 M NaOH (6 mL) and stirred for 45 minutes. The dark mixture was diluted with ethyl acetate and acidified with 1.0 N HCl. The layers were separated and the organics washed successively with water, 0.5 M NaHCO3, water, brine and dried (MgSO4). The mixture was filtered, evaporated and the residue was purified on silica gel (hexane:ethyl acetate 4:1) to give 0.55 g of 3-(2-methoxyphenyl)-4,5-methylenedioxyphenol (68%) as a tan solid, 1H NMR (500 MHz; CDCl3): δ 3.82 (s, 3H); 5.91 (s, 2H); 6.40–6.45 (m, 2H); 6.99 (d, J=9.0 Hz, 1H); 7.02 (d, J=7.0 Hz, 1H); 7.40–7.30 (m, 2H).

Provenance & Evidence