4-(Benzyloxy)-2-nitrophenol → 2-Amino-4-(benzyloxy)phenol

Participants

Reaction Steps

50 g. 4-benzyloxy-2-nitrophenol [U.S. Pat. No. 4,603,2091] (Compound XXII) is dissolved in 100 mL dimethylformamide to give a yellow solution which is shaken in the presence of 5% platinum on charcoal under 40 psi pressure of hydrogen. After 12 hours, the reduction is colorless and is filtered through diatomaceous earth to remove the catalyst. The clear filtrate is diluted to 800 mL with ethyl acetate and is washed three times with 500 mL water. The organic layer is evaporated to yield a clear oil, which is triturated with cold methanol and filtered to give 4-benzyloxy-2-aminophenol as a gray solid (Compound XXIII).

Provenance & Evidence