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

HRID 1909324Notes

Reaction equation

HRID 1909324 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].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 820095-Chloro-2-methylbenzoic acid

Product 1

HCID 230097625-Chloro-2-methyl-3-nitrobenzoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A stirred solution of 5-chloro-2-methylbenzoic acid (1 mmol) in conc. H2SO4 (2 mL) was cooled to −10° C. and nitrating mixture (0.4 mL of conc. H2SO4+0.1 mL of conc. HNO3) was added to it in dropwise manner. The reaction mixture was stirred at the same temperature for 20 min then warmed to room temperature. The solid precipitate was filtered and dried to obtain 5-chloro-2-methyl-3-nitrobenzoic acid which was used in next step without further purification (yield 60-70%).

Workup

  1. filtrationThe solid precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-3e4b8b928c9e44219b00d15ad4af0d03
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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