Methanol → Methyl 4-chloro-2-methoxy-5-nitrobenzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:6]([OH:8])=[O:7].S(=O)(=O)(O)O.[CH3:21]O>>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:6]([O:8][CH3:21])=[O:7]Participants
4
Procedure
To a solution of 3.1 g of 4-chloro-5-nitro-o-anisic acid in methanol (100 ml) was added a catalytic amount of sulfuric acid and the resulting mixture was heated under reflux for 3 hours. Then the reaction mixture was poured into ice/water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 3.3 g of methyl 4-chloro-5-nitro-o-anisate was obtained as pale yellow crystals.