Water → Methyl 3-chloro-p-anisate

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To a solution of 3-chloro-4-hydroxybenzoic acid (3.45 g, 20 mmol) in N,N-dimethylformamide (10 mL) were added potassium carbonate (6.9 g, 50 mmol) and methyl iodide (large excess) and the mixture was stirred at 60° C. for 2 h. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give an almost pure title compound (4.0 g, 100%).

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