Nitric Acid → 2,4,6-Trichloro-3-nitrobenzoic acid

HRID 1899967Notes

Reaction equation

HRID 1899967 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[C:7]=1[C:8]([OH:10])=[O:9]>S(=O)(=O)(O)O>[Cl:5][C:6]1[C:14]([N+:1]([O-:4])=[O:2])=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 57642,4,6-Trichlorobenzoic acid

Product 1

HCID 105400022,4,6-Trichloro-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Concentrated sulfuric acid (2.8 ml) was added dropwise to 70% nitric acid (4.0 ml) in an ice-water bath. This mixture was added to a solution of 2,4,6-trichlorobenzoic acid (5.13 g) in concentrated sulfuric acid (23 ml) dropwise for 20 minutes in an ice-water bath. The mixture was stirred for 16 hours at ambient temperature and poured into ice-water (300 ml) slowly. This mixture was stirred for 1 hour at ambient temperature. The precipitate was collected by vacuum filtration and washed with water to give 2,4,6-trichloro-3-nitrobenzoic acid (5.26 g) as colorless fine crystals.

Workup

  1. stirringThis mixture was stirred for 1 hour at ambient temperature
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-3dba78f0c811444ea42d57c249e248dd
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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