Nitric Acid → 4-Chloro-3-nitrobenzoic acid

HRID 1763060Notes

Reaction equation

HRID 1763060 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[N+:16]([O-])([OH:18])=[O:17]>O>[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 944Nitric Acid3×HCID 1118Sulfuric AcidHCID 63184-Chlorobenzoic Acid

Product 1

HCID 73204-Chloro-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 5-liter, 3-necked, round-bottom flask, equipped with a stirrer and thermometer, is added 2.0 liters of concentrated H2SO4 and 800 g of powdered (about 1-2 microns) p-chlorobenzoic acid. The mixture is stirred and cooled to 0° C. in an oil bath. To the cooled mixture is added 432 ml of 71 weight percent nitric acid in water solution dropwise. The nitric acid solution is added at a rate slow enough to maintain the temperature lower than about 30° C. Upon completion of adding nitric acid, the temperature is raised to 37° C. over 3 hours. The reaction mixture is then cooled to 15° C. To the cooled mixture is added 0.75 liter of room temperature water at a rate so as to keep the reaction temperature below about 40° C. The product is isolated by filtration using fritted glass funnel and washed with 1.5 liters of room temperature water. The washed product is air-dried until a constant weight is observed to yield 1.0174 kg of 4-chloro-3-nitrobenzoic acid, which has a melting point of 178° C.-179.5° C. This is a yield of 99 mole percent. This material can be used without further purification.

Workup

  1. customTo a 5-liter, 3-necked, round-bottom flask, equipped with a stirrer
  2. temperatureto maintain the temperature lower than about 30° C
  3. temperatureThe reaction mixture is then cooled to 15° C
  4. customthe reaction temperature below about 40° C
  5. customThe product is isolated by filtration
  6. washwashed with 1.5 liters of room temperature water
  7. customThe washed product is air-dried until a constant weight

Sources & evidence

ORD record
ord-08a1bc94393441559be3f65319c4acb3
Source dataset
uspto-grants-1989_05
Patent number
US04835306

Reaction notes

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