Benzyl Chloride → 3-Iodobenzyloxybenzene

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To a suspension of 60% sodium hydride (20 g, 0.5 mol) in dimethylformamide (300 ml), a solution of m-iodophenol (100 g, 0.454 mol}in dimethylformamide was added dropwise and then stirring was continued for 30 min at 70°±5° C. To this reaction mixture, benzyl chloride (57.4 g, 0.454 mol) was added dropwise and the reaction was continued for 2 hours at 100°±5° C. The resultant mixture was taken up in H2O (1l) and extracted with ethyl acetate. The organic extract was washed with H2O, dried over anhydrous MgSO4 and then evaporated. The residual solid was recrystallized from ethanol to give the title compound as white crystals; yield: 119.7 g; mp. 51.0°-53.0° C.

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