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

HRID 2208752Notes

Reaction equation

HRID 2208752 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].[N+:17]([O-])([OH:19])=[O:18]>>[Cl:6][C:7]1[CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]([CH3:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13]

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 93%

Procedure

To a stirred ice cold (−10 to −15° C.) conc. H2SO4 (136 mL) was added 5-chloro-2-methylbenzoic acid (20 g, 0.117 mmol) in portions. The nitrating mixture [Conc. H2SO4 (22 mL) and HNO3 (11.05 mL] was added dropwise at −10 to −15° C. and resulting mixture was allowed stir for 30 min. The obtained precipitate was filtered and dried. The solid was the dissolved in ethyl acetate and dried (Na2SO4) and concentrated to provide desired product (23.6 g, 93%) as a white solid.

Workup

  1. customresulting mixture
  2. filtrationThe obtained precipitate was filtered
  3. customdried
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b4666ef96a994b7baff125e00b97d8f1
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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