Nitric Acid → 5-Chloro-2-methyl-3-nitrobenzoic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[N+:17]([O-])([OH:19])=[O:18]>>[Cl:1][C:2]1[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]Participants
4
Conditions
- Temperature
- -10 °C
Procedure
5-chloro-2-methylbenzoic acid (4.0 g, 23 mmol) was added portionwise to cooled conc. H2SO4 (27 mL) at −10° C. After 10 minutes a nitrating mixture {prepared by mixing conc. HNO3 (3.3 g, 52.68 mmol) with conc. H2SO4 (4.4 mL)} was added dropwise at −10° C. The resulting reaction mass was stirred at −10° C. for 30 minutes. On completion, the reaction mixture was poured on ice cold water, the solid precipitate was filtered, washed with water and dried under vacuum giving the title compound (4.95 g, 99%).
Workup
- customAfter 10 minutes a nitrating mixture {prepared
- additionwas added dropwise at −10° C
- customThe resulting reaction mass
- additionOn completion, the reaction mixture was poured on ice cold water
- filtrationthe solid precipitate was filtered
- washwashed with water
- customdried under vacuum
Sources & evidence
- ORD record
- ord-e820b30a364b4eb5bd07677deca44969
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376422B2
Reaction notes
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