Nitric Acid → 2,6-Dimethyl-3-nitrobenzoic acid

HRID 613602

Reaction equation

HRID 613602 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:10]([N+:12]([O-:14])=[O:13])=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 124392,6-Dimethylbenzoic acid

Product 1

HCID 2393292,6-Dimethyl-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent3×

Procedure

To a solution of 2,6-dimethylbenzoic acid (20 g) in conc. sulfuric acid (100 ml) was dropwise added under ice-cooling a mixture of 70% nitric acid and conc. sulfuric acid (21.6 ml), which was prepared by dropwise adding conc. sulfuric acid (10.8 ml) to 70% nitric acid (15.1 ml) under ice-cooling, and the mixture was stirred for 1 hour at the same temperature. Ice-water was added to the reaction mixture, and the resulting precipitates were filtered off. The filtrate was concentrated, and the residue was purified by flash chromatography (dichloromethane:methanol=20:1 including 1% acetic acid) to give 2,6-dimethyl-3-nitrobenzoic acid (7.0 g) as a colorless crystal.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe resulting precipitates
  4. filtrationwere filtered off
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography (dichloromethane:methanol=20:1 including 1% acetic acid)

Sources & evidence

ORD record
ord-c3c46dd4647545a290c63038c2f0b387
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Linked notes

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