Acetic Acid → 4-Methyl-2-nitrobenzoic acid

HRID 274588

Reaction equation

HRID 274588 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8]C=1C#N)([O-:3])=[O:2].[C:13]([OH:16])(=[O:15])[CH3:14]>S(=O)(=O)(O)O>[CH3:12][C:10]1[CH:9]=[CH:8][C:14]([C:13]([OH:16])=[O:15])=[C:4]([N+:1]([O-:3])=[O:2])[CH:11]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 962352-Nitro-4-toluonitrile

Product 1

HCID 2550274-Methyl-2-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixed solution of 2-nitro-4-methylbenzonitrile (15.8 g) in a mixture of 65% sulfuric acid and acetic acid (150 ml) was heated under reflux for 17 hours. After concentration, the residue was poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. Recrystallization of crystals from ether-hexane afforded colorless crystals (16.5 g, 94%), m.p. 156°-157° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hours
  3. concentrationAfter concentration
  4. additionthe residue was poured into ice-water
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. customRecrystallization of crystals from ether-hexane afforded colorless crystals (16.5 g, 94%), m.p. 156°-157° C.

Sources & evidence

ORD record
ord-3db63667ac724b178f81ecd389f3541d
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Linked notes

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