Hydroxyamine hydrochloride → 1-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]-N-hydroxyethanimine

Participants

Reaction Steps

A stirred solution of 1-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]ethanone (15 g, 32 mmol), NH2OH.HCl (3 g, 42 mmol) and CH3COONa (3.5 g, 42 mmol) in ethanol (150 mL) and acetic acid (250 mL) was refluxed for 5 hours. The solvent was removed and the residue taken up in ethyl acetate was thoroughly washed with 2 M NaHCO3 solution then with brine. After drying over Na2SO4, the solvent was removed and the oily residue was filtered on a small pad of silica gel eluting with hexane/ethyl acetate 6/3 to provide the title compound (13.3 g, 88% yield).

Provenance & Evidence