Nitric Acid → 4-Chloro-3-nitrobenzoic acid

HRID 259087Notes

Reaction equation

HRID 259087 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[N+:11]([O-])([OH:13])=[O:12].S(=O)(=O)(O)O.O>ClCCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 63184-Chlorobenzoic Acid

Product 1

HCID 73204-Chloro-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

78.25 g of 4-chlorobenzoic acid were suspended in 400 ml of 1,2-dichloroethane. 99.0 g of a mixed acid containing 35.2% of nitric acid and 64.2% of sulphuric acid were added dropwise with stirring over a period of 3 hours at 40° C. After stirring for 2 hours at that temperature, the reaction mixture was poured on to 300 ml of water. The 1,2-dichloroethane was then distilled off and the reaction product filtered off from the residual aqueous suspension, washed with water and dried at 90° C., giving 97.8 g (96.8% of the theoretical) of 4-chloro-3-nitrobenzoic acid melting at 182.9° to 184.0° C. with a purity of 99.5%. The content of unreacted 4-chlorobenzoic acid amounted to only about 0.1%.

Workup

  1. additionwere added dropwise
  2. stirringAfter stirring for 2 hours at that temperature
  3. distillationThe 1,2-dichloroethane was then distilled off
  4. filtrationthe reaction product filtered off from the residual aqueous suspension
  5. washwashed with water
  6. customdried at 90° C.

Sources & evidence

ORD record
ord-bcf47a81f63b43b7b1d3112d2afd977a
Source dataset
uspto-grants-1977_07
Patent number
US04036838

Reaction notes

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