Benzyl Bromide → 3-Benzyloxy-4-hydroxymethylbenzonitrile

Participants

Reaction Steps

33.1 g of 4-formyl-3-hydroxybenzonitrile (Liebigs Ann. Chem. (1982) 1836) were O-benzylated with 1 eq. each of benzyl bromide and K2CO3 and, after workup, reduced with NaBH4 in 100 ml of MeOH/THF 2:3 at -10° C. to 0° C. to give the alcohol. 22.4 g were obtained. The product could be crystallized from DCM/petroleum ether. 1H-NMR (CDCl3, δ in ppm): 7.48 (1H), 7.40-7.3 (5H), 7.20 (1H), 7.08 (1H), 5.05 (s, 2H), 4.75 (s, 2H), 2.85 (1H, OH)

Provenance & Evidence