2-Chloro-4-nitrobenzoic acid → Benzoyl chloride, 2-chloro-4-nitro-

HRID 2295374Notes

Reaction equation

HRID 2295374 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9]>>[Cl:5][C:6]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:7]=1[C:8]([Cl:3])=[O:9]

Participants

3

Reactant 2

HCID 74482-Chloro-4-nitrobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 81522Benzoyl chloride, 2-chloro-4-nitro-Yield 93.4%

Procedure

In accordance with Method II, thionyl chloride (800 g, 6.72 m) was added to 2-chloro-4-nitrobenzoic acid (500 g, 2.48 m) while the reaction mixture was warmed. After addition, the mixture was refluxed for approximately three hours. The excess thionyl chloride was removed by distillation and the remaining reaction mixture was vacuum-distilled to yield 2-chloro-4-nitrobenzoyl chloride (510 g, 93% bp 143° C./4 mm).

Workup

  1. temperaturewas warmed
  2. additionAfter addition
  3. temperaturethe mixture was refluxed for approximately three hours
  4. customThe excess thionyl chloride was removed by distillation
  5. customthe remaining reaction mixture
  6. distillationwas vacuum-distilled

Sources & evidence

ORD record
ord-deee18049efe4e5b84371673d012b112
Source dataset
uspto-grants-1984_01
Patent number
US04424371

Reaction notes

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