Nitric Acid → 4-Chloro-2-methyl-3-nitrobenzoic acid

HRID 1639810Notes

Reaction equation

HRID 1639810 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:15])[CH:7]=1>>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:15])[C:7]=1[N+:1]([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 3482694-Chloro-2-methylbenzoic acid

Product 1

HCID 107039094-Chloro-2-methyl-3-nitrobenzoic acidYield 97.2%

Conditions

Temperature
7.5 °C

Procedure

To fuming nitric acid (20.4 mL, 410 mmol) was slowly added dropwise 4-chloro-2-methylbenzoic acid (5.0 g, 29.3 mmol) while maintaining the temperature of the reaction mixture at 5-10° C. The reaction solution was stirred at 0-5° C. for 1 hr, and poured into ice. The precipitated solid was recovered, washed with water, and dried under reduced pressure to give 4-chloro-2-methyl-3-nitrobenzoic acid (6.14 g, purity 33%) as a crudely purified product.

Workup

  1. additionpoured into ice
  2. customThe precipitated solid was recovered
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-dae83945460e44f7b0017e4b9b7345df
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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