Benzyl Alcohol → Benzyl chloromethyl ether

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)

1. customwas bubbled into the reaction mixture
2. customReaction progress
3. customWhen the starting material had been consumed
4. customN2 was bubbled through the reaction mixture
5. customto remove HCl gas
6. customThe mixture was partitioned between water and n-pentane
7. dry with materialThe organic layer was dried over MgSO4
8. concentrationconcentrated
9. distillationdistilled under vacuum

ORD record

ord-ce2888b96bf94392b027fc1401fa22cb

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084485B2