Nitric Acid → Methyl 5-chloro-2-hydroxy-3-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

Methyl-5-Chloro-2-hydroxylbenzoate (30 g, 160 mmol) is suspended in sulfuric acid (140 mL) and cooled to 0° C. in an ice bath. Nitric acid (13 mL) in sulfuric acid (30 mL) is added drop wise to the suspension over 30 minutes while maintaining the reaction temperature at 0° C. The reaction is warmed to room temperature and stirred for 4 hours. An additional 6 mL of nitric acid is added drop wise to the reaction over 30 minutes and the reaction is heated to 45° C. for 16 hours. The reaction is poured onto crushed ice, and the resulting yellow precipitate collected and washed with copious amount of water and dried in vacuo to give the title compound (33 g 142 mmol, 89%). LCMS (ESMS): m/z 232.7 (M+H+).

Provenance & Evidence