3-Hydroxy-2-naphthoic acid → 2-Naphthalenecarboxylic acid, 4-chloro-3-hydroxy-

Participants

Reaction Steps

The chilled sodium hypochlorite solution is added to the chilled solution of 2-hydroxy-3-naphthoic acid, keeping the temperature below 10° C. When the addition of sodium hypochlorite is completed, the reaction mixture is held at about 10° C. for 2 hours and then heated to the boil. To this solution is then added 250 ml of 14.1% hydrochloric acid. The resulting slurry of deep yellow solid material is heated to the boil and then cooled to ambient temperature. The slurry is filtered, washed with 2 liters of water and dried to constant weight. There is obtained 52.6 grams of 1-chloro-2-hydroxy-3-naphthoic acid (purity 97.2% by HPLC) representing a yield of 91.8% of theoretical.

Provenance & Evidence