[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1.Cl[CH2:14][C:15]([OH:17])=[O:16].Cl>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][C:15]([OH:17])=[O:16])=[C:6]([O:11][CH3:12])[CH:5]=1To a solution of sodium hydroxide (6.6 g, 160 mmol) in water (45 mL) was added 4-chloro-2-methoxy-phenol (2.0 mL, 16 mmol) and chloroacetic acid (7.7 g, 81 mmol). The resulting mixture was heated to 95° C. and stirred for three hours. The reaction was allowed to cool to ambient temperature and slowly acidified with concentrated hydrochloric acid (10 mL) until the mixture became a solution and then extracted with diethyl ether. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (4.16 g).
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