Potassium Hydroxide → 5-Amino-2-methylphenol

Participants

Reaction Steps

In the hydrogenolysis step, 8.0 g (38 mmol) of 5-acetamido-2-[(N,N-dimethylamino)methyl]phenol was dissolved in 54 ml (162 mmol) of 3N potassium hydroxide solution in a Parr bottle. Palladium on activated carbon (0.8 g; 3% Pd/C) was added to the solution. The reaction mixture was shaken under hydrogen on a Parr apparatus for 3 hours at 70°-80° C. and 60 psi. The catalyst (Pd/C) was removed by filtration and the filtrate brought to about pH 12 with 6M HC1 (15-20 ml). The off-white crystalline product precipitated out of solution. The solution was cooled and the precipitate filtered, washed with water, and dried overnight in a vacuum oven to give 3.2 g (68% yield) of 5-amino-o-cresol, m.p. 158°-160° C.). The purity of 5-amino-o-cresol prepared by this procedure was determined to be 97% by perchloric acid titration.

Provenance & Evidence