3-Amino-4-methylbenzonitrile → 3-Hydroxy-4-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 49.2 g (0.72 mol) of NaNO2 in 217 ml of water was added dropwise over the course of 30 min to 85 g (0.72 mol) of 3-amino-4-methylbenzonitrile in 1.8 l of 6N HCl at 0-5° C. The mixture was then stirred at 0-5° C. for a further 30 min and then at the boiling point for 1 h. After the solution had cooled it was possible to extract the product with ethyl acetate and, from this, the phenolate with ice-cold 5N NaOH. The aqueous phase was then acidified to pH 3 with 6N HCl and the product was extracted with ethyl acetate. 41 g (43%) of the phenol were obtained. 1H-NMR (DMSO-d6; δ in ppm): 10.3 (s, OH); 7.25 (dd, 1H); 7.15 (d, 1H); 7.1 (dd, 1H); 2.20 (s, 3H)

Provenance & Evidence