Hydrochloric Acid → 4-Methyloxybenzyl chloride

Participants

Reaction Steps

4-Methoxybenzylalcohol (50 g, 0.36 mol) (Aldrich) was added dropwise to 100 mL of conc. HCl and stirred vigorously for 2 h at rt. The reaction mixture was extracted four times with Et2O, the Et2O extracts were combined, washed with brine, dried (Na2SO4), and concentrated. The yellow oil was distilled at 70°-73° C. (0.2 mmHg) to give 52 g (93%) as a colorless oil: 1H NMR (CDCl3) d 3.85 (s, 3H, OCH3), 4.62 (s, 2H, CH2Cl), 6.91-6.93 (d, 2H, J=8 Hz, ArH), 7.38-7.40 (d, 2H, J=8 Hz, ArH) ; MS(FD) 156(M+).

Provenance & Evidence