Sodium Hydroxide → 4-Fluoro-2-methoxy-5-morpholin-4-yl-benzoic acid
Reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:7]([F:16])=[CH:6][C:5]=1[O:17][CH3:18].[OH-].[Na+]>C(O)C>[F:16][C:7]1[C:8]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[CH:9][C:4]([C:3]([OH:19])=[O:2])=[C:5]([O:17][CH3:18])[CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).