Sulfuric Acid → 2-Chloro-4-hydroxybenzonitrile

Participants

Reaction Steps

The 2-chloro-4-aminobenzonitrile (57 g, 0.37 m) was added to a cold stirred solution of concentrated sulfuric acid (115 g) in water (1,000 ml). Then a cold solution of sodium nitrite (26.5 g, 0.38 m) in water (250 ml) was added to the suspension solution at a temperature between 0° and 6° C. Upon addition of the sodium nitrite, stirring continued for approximately three hours at which time urea (3 g) was added to the reaction mixture. The reaction mixture reacted at a temperature between 69° and 76° C. for approximately three hours. The reaction product was filtered and crystallized from water to yield the fifth step product 2-chloro-4-hydroxybenzonitrile (18.8 g, 33%, mp 157°-158° C.).

Provenance & Evidence