[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)[C:6]([O:8]C)=[O:7].Cl.O>[OH-].[Na+].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)[C:6]([OH:8])=[O:7]A mixture of methyl 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzoate (16.0 g) in 2N aqueous sodium hydroxide solution (65 mL) and methanol (100 mL) was stirred at room temperature for 1 hr, and the mixture was acidified with 6N hydrochloric acid (pH=3-4). Water was added to the reaction mixture, and the precipitate was collected by filtration. The solid was washed with ethyl acetate and water to give the title compound (8.07 g). To the filtrate was added saturated brine, and the mixture was extracted with ethyl acetate/2-propanol. The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate to give the title compound (4.10 g).
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