Hydrazine hydrate (1:1) → 4-Amino-3,5-dimethylphenol

Participants

Reaction Steps

3,5-Dimethyl-4-phenylazophenol (132.0 g, 0.583 mol) was dissolved in methanol (500 mL) and pure (100%) hydrazine hydrate (113 mL, 2.33 mol), and Raney nickel [50% slurry in water (Aldrich), (2.5 mL)] was added to give an exothermic reaction. The mixture was stirred for one hour at ambient temperature and then heated to gentle reflux for three hours. The solution was filtered hot and cooled to room temperature. The crystals which formed were collected by filtration and dried to afford 3,5-dimethyl-4-aminophenol (42.4 g, 60% yield) as a white solid; m.p. 180.5-182.5; 1H-NMR (DMF-d7). δ 2.10 (s, 6H, CH3), 5.32 (s, 2H, NH2), 5.32 (s, 1H, OH), 6.45 (s, 2H, aromatic).

Provenance & Evidence