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

HRID 2295369Notes

Reaction equation

HRID 2295369 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 I, halogenating agent 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 of the low-boiling thionyl chloride was removed by distillation and the residue 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 of the low-boiling thionyl chloride was removed by distillation
  5. customthe residue reaction mixture
  6. distillationwas vacuum-distilled

Sources & evidence

ORD record
ord-a05536efe676472e820e2a45ec7e5b55
Source dataset
uspto-grants-1984_01
Patent number
US04424371

Reaction notes

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