[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5](=[CH:9][C:10]=1[N+:13]([O-:15])=[O:14])[C:6]([OH:8])=[O:7]To a solution of 33 g of 4-chloro-o-anisic acid in sulfuric acid (100 ml) was added 20 g of potassium nitrate under ice-cooling and the resulting mixture was stirred for 2 hours. The reaction mixture was added to ice/water and extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 41 g of the title compound was obtained as pale yellow crystals.
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