Nuceophilic substitution of a benzylic alcohol

SyntheticPage 518
Published Nov 21, 2011


Reaction Scheme

Procedure

A mixture of p-methoxybenzyl alcohol (41.40 g, 0.30 mol) and hydrochloric acid (37%; 75 mL, 0.90 mL) was stirred for 30 min at room temperature. The product was extracted with petroleum ether (40 mL), the extract washed with water (3 × 50 mL), dried over anhydrous sodium sulfate and the solvent removed under reduced pressure to give p-methoxybenzyl chloride as a colorless oil (45.35 g, 97% yield).

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