Hydrochloric Acid → 2-Methyl-6-[3-(quinolin-2-ylmethoxy)-phenoxymethyl]-benzoic acid

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Reaction Steps

A solution of methyl 2-methyl-6-[3-(quinolin-2-ylmethoxy)-phenoxymethyl]-benzoate (1.6 g, 3.8 mmol, example 4) in ethanol (25 mL) is heated with a 10N sodium hydroxide solution (4.0 mL, 40 mmol) at 70° C. for 14 h. The reaction is cooled, neutralized with a 2N HCl solution (20 mL) and concentrated to remove the ethanol. Ethyl acetate is added and washed with water. The aqueous layer is saturated with sodium chloride and back extracted with ethyl acetate. The organic layers are combined, dried over magnesium sulfate, filtered and concentrated to yield a crude solid. The solid is purified by column chromatography (silica, 5 to 10% methanol in dichloromethane) to provide the title compound. An analytically pure sample is prepared by recystallization from methanol: m.p. 167–168° C., 1H NMR (300 MHz, CDCl3)δ0.15 (d, 2H), 7.80 (d, 1H), 7.71 (t, 1H), 7.61–7.51 (m, 2H), 7.26–7.10 (m, 3H), 7.00 (t, 1H), 6.66 (s, 1H), 6.52 (d, 1H), 6.46 (d, 1H), 5.26 (s, 2H), 5.15 (s, 2H), 2.44 (s, 3H); MS (ESI) 400 (M+H)+.

Provenance & Evidence