3-Hydroxy-2-naphthoic acid → 2-Naphthalenecarboxylic acid, 4-chloro-3-hydroxy-
Reaction equation
[Cl:1][O-].[Na+].[OH:4][C:5]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1>Cl>[Cl:1][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:14]([C:15]([OH:17])=[O:16])[C:5]=1[OH:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.