Nitric Acid → 4-Chloro-3-nitrobenzoic acid

HRID 259086Notes

Reaction equation

HRID 259086 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>C(Cl)Cl>[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 6344DichloromethaneSolvent

Conditions

Temperature
42 °C

Procedure

78.25 g (0.5mol) of 4-chlorobenzoic acid were suspended in 200 ml of methylene chloride, followed by the addition with stirring at room temperature of 33.5 g (0.55 mol) of 98% nitric acid. The mixture was heated with stirring to boiling temperature, followed by the dropwise addition over a period of 1 hour at that temperature of 63.5 g of 100% sulphuric acid. After cooling to 42° C., the mixture was stirred for 2 hours at that temperature. The reaction mixture was then poured onto 300 ml of water, and the methylene chloride subsequently distilled off. The residual suspension was filtered, the residue washed with water and dried at 90° C., giving 98.4 g (97.3% of the theoretical yield) 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. additionfollowed by the addition
  2. temperatureThe mixture was heated
  3. stirringthe mixture was stirred for 2 hours at that temperature
  4. distillationthe methylene chloride subsequently distilled off
  5. filtrationThe residual suspension was filtered
  6. washthe residue washed with water
  7. customdried at 90° C.
  8. customgiving 98.4 g (97.3% of the

Sources & evidence

ORD record
ord-1ffc9e38b37c4acda31d57898dc907f5
Source dataset
uspto-grants-1977_07
Patent number
US04036838

Reaction notes

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