Benzyl Alcohol → Benzyl chloromethyl ether

Participants

Reaction Steps

Paraformaldehyde (152 g) power was added to stirred benzyl alcohol (750 g, 6.94 mol), and HCl gas was bubbled into the reaction mixture. The exhaust gas was scrubbed with conc aq NaOH. Reaction progress was monitored by 1H NMR. When the starting material had been consumed, N2 was bubbled through the reaction mixture to remove HCl gas. The mixture was partitioned between water and n-pentane. The organic layer was dried over MgSO4, concentrated, and distilled under vacuum to afford ((chloromethoxy)methyl)benzene boiling at 60-63° C. (350 g, 33%). 1H NMR (400 MHz, CDCl3): 4.76 (s, 2H), 5.54 (s, 2H), 7.36 (m, 5H)

Provenance & Evidence