Hydrochloric Acid → 3-Hydroxy-4-methylbenzonitrile

Participants

Reaction Steps

Into a reaction vessel was charged 4-cyano-2-aminotoluene (13) (132.0 g, 1.0 mol) and 6 N hydrochloric acid aqueous solution (800 ml), and an aqueous solution obtained by dissolving ice-cooled sodium nitrite (76.0 g, 1.1 mol) in water (320 ml) was dropped over 1.5 hours, further, the solution was stirred for approximately 20 hours under ref lux. To the reaction liquid was added toluene and extracted, then, a sodium hydroxide aqueous solution was added to the toluene layer to make the aqueous layer alkaline. The resulted aqueous layer was acidified with concentrated hydrochloric acid, then, extracted with ethyl acetate. The resulted ethyl acetate layer was washed with saturated saline, dried, and the solvent was distilled off under reduced pressure, to obtain 4-cyano-2-hydroxytoluene (14) (91.6 g, yield from (13) is 69%).

Provenance & Evidence