2-(4-Nitrophenoxy)ethanol → 2-(4-Aminophenoxy)ethanol

Participants

Reaction Steps

2-(4-Nitrophenoxy)ethanol (1.83 g, 10 mmol) was dissolved in EtOH (100 mL) under air at RT. A catalytic amount of 10% Pd/C was added. The air was replaced with a H2(g) atmosphere and the reaction was stirred vigorously for 18 h. The reaction was quenched by filtering it through Celite® with EtOH. The filtrate was concentrated under reduced pressure and the recovered material was purified by eluting it through a 17×2.5 cm column of silica gel (5% and 10% MeOH/CH2Cl2 step gradient) giving 2-(4-amino-phenoxy)ethanol as a black solid: MS m/z 154=[M+H]+. Calc'd for C8H11NO2: 153.08.

Provenance & Evidence