Sodium Hydroxide → 4-Fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid

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Reaction Steps

A suspension of 4-fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid methyl ester (1.20 g, 4.46 mmol) in ethanol (22.0 mL) was treated with aq 2 N NaOH (13 mL, 26.7 mmol). The mixture was stirred at room temperature for 2 h, concentrated until most of the ethanol was removed and acidified with aq 2 N HCl to pH 1. After extracting with ethyl acetate, the organic layer was washed with saturated aq NaCl, dried over MgSO4 and concentrated to give-4-fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid (0.90 g, 79%): 1H NMR (DMSO-d6 300 MHz) δ 12.62 (s, 1 H), 7.34 (d, J=10.5 Hz, 1 H), 7.04 (d, J=14.7 Hz, 1 H), 3.76 (s, 3 H), 3.70 (t, J=4.7 Hz, 4 H), 2.90 (t, J=4.7 Hz, 4 H).

Provenance & Evidence