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

HRID 2208695Notes

Reaction equation

HRID 2208695 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%

Conditions

Temperature
-10 °C

Procedure

5-Chloro-2-methylbenzoic acid (4 g, 23.39 mmol) was added to cooled conc. H2SO4 (27 mL) at −10° C. lot wise. After 10 minutes nitrating mixture {prepared as mixing Conc. HNO3 (3.3 g, 52.68 mmol) with conc.H2SO4 (4.4 mL)} was added drop wise at −10° C. Resulting reaction mass was stirred at −10° C. for 30 minutes. On completion, reaction mixture was poured on ice cold water, solid precipitated was filtered, washed with water and dried under vacuum giving desired compound (4.95 g, 99%).

Workup

  1. custommixture {prepared
  2. customResulting
  3. customreaction mass
  4. customOn completion, reaction mixture
  5. additionwas poured on ice cold water, solid
  6. customprecipitated
  7. filtrationwas filtered
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-6ea71058d6f1488387414d221eda3823
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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