Benzene → 4-Benzyloxybenzyl chloride

In a 1 l four-necked flask, there were placed 85.4 g (0.464 mole) of benzyl phenyl ether, 45 g (1.5 moles) of paraformaldehyde, 300 ml of conc. hydrochloric acid and 100 ml of benzene, and the resulting mixture was stirred for 4 hours at 50° to 60° C. After completion of the reaction, 100 ml of toluene was added to the resulting reaction mixture followed by vigorous stirring of the resulting mixture. The resulting organic layer in the mixture was washed twice with 200 ml of water. The thus obtained organic layer was dried over anhydrous sodium sulfate followed by removal of the solvent by evaporation. To the so obtained viscous oily substance were added about 200 ml of n-heptane and 50 ml of ethyl ether. Upon stirring of the resulting mixture at room temperature, crystals precipitated. After allowing the mixture to stand overnight, the crystals were collected by filtration and dried to give 30.5 of 4-benzyloxybenzyl chloride.