m-Nitroacetophenone → 1-(3-Aminophenyl)ethanol

Participants

Reaction Steps

Following the procedure of Example I m-nitroacetophenone (82.5 g., 0.50 mole; 99% purity by GLC), water (300 ml.), and Raney nickel catalyst (27 g. (wet), Grace No. 4200) charged to a 1 liter Parr stirring autoclave. The hydrogen pressure was 50 psi initially and allowed to decrease to 40 psi whereupon the pressure was raised to 50 psi and again allowed to decrease as hydrogenation continued. The temperature was slowly raised from 25° C to 100° C. After 61/2 hours, hydrogen absorption apparently ceased. Work-up as in example I gave 26.5 g. m-amino-α-methylbenzyl alcohol (38.7% yield) which was 100% pure by GLC and a residue of 38.1 g. which contained 87.2% m-amino-α-methylbenzyl alcohol and 12.8% m-aminoacetophenone.

Provenance & Evidence