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

HRID 2208791Notes

Reaction equation

HRID 2208791 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 99.8%

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 the nitrating mixture {consisting of concentrated HNO3 (3.3 g, 52 mmol) and concentrated H2SO4 (4.4 mL)} was added dropwise at −10° C. The mixture was stirred at −10° C. for 30 minutes and poured on ice cold water. The solid precipitate was filtered, washed with water and dried under vacuum to give the title compound (4.95 g, 99%).

Workup

  1. additionwas added dropwise at −10° C
  2. additionpoured on ice cold water
  3. filtrationThe solid precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4cfac51528d94c498d8de5e9e5ab9650
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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