Nitric Acid → 5-Chloro-2-methyl-3-nitrobenzoic acid

HRID 2208692Notes

Reaction equation

HRID 2208692 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

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 820095-Chloro-2-methylbenzoic acid

Product 1

HCID 230097625-Chloro-2-methyl-3-nitrobenzoic acidYield 99%

Procedure

5-chloro-2-methylbenzoic acid (4 g, 23.4 mmol) was added to cooled conc. H2SO4 (27 mL) at −10° C. in small portions and stirred for 10 minutes. Nitrating mixture {prepared by mixing Conc. HNO3 (3.3 g, 52.68 mmol) with conc.H2SO4 (4.4 mL)} was added drop wise at −10° C. The resulting mixture was stirred at −10° C. for 30 minutes. On completion, the reaction mixture was poured into ice cold water, the solid was collected by filtration, washed with water and dried under vacuum to give 5-chloro-2-methyl-3-nitrobenzoic acid (4.95 g, 99%).

Workup

  1. customNitrating mixture {prepared
  2. stirringThe resulting mixture was stirred at −10° C. for 30 minutes
  3. additionOn completion, the reaction mixture was poured into ice cold water
  4. filtrationthe solid was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-69fb353dab9b4cbcabf522cfdd9573aa
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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