Methanol → 2-[5-Chloro-2-hydroxy benzyl]isoindole-1,3-dione

To 4-chlorophenol (2.0 g, 15.5 mmol) and chloromethylphthalamide (2.62 g, 13.4 mmol) was added zinc chloride (3 mL, 0.5 M in tetrahydrofuran, 1.5 mmol). The reaction was stirred at 90° C. for 48 hours. After cooling the reaction was diluted with methanol (15 mL) and brought to reflux. After 30 minutes the hot suspension was filtered through a medium glass frit and concentrated to an off-white solid. Methanol (50 mL) was again added and the reaction brought to reflux. After 3 hours the hot suspension was filtered through a medium glass frit and concentrated to an off-white solid. The crude product was purified via chromatography on silica gel to give the title compound (3.86 g).