2,3,4,5-Tetrachlorobenzoic acid → 2,3,4,5-Tetrachlorobenzoyl chloride

HRID 1607951Notes

Reaction equation

HRID 1607951 reaction equation
[Cl:1][C:2]1[C:3]([Cl:13])=[C:4]([Cl:12])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)([Cl:16])=O>>[Cl:1][C:2]1[C:3]([Cl:13])=[C:4]([Cl:12])[C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([Cl:16])=[O:8]

Participants

3

Reactant 2

HCID 57822,3,4,5-Tetrachlorobenzoic acidHCID 24386Thionyl Chloride2×

Product 1

HCID 54637972,3,4,5-Tetrachlorobenzoyl chloride

Procedure

The desired tetrachlorobenzoyl chloride is prepared by reacting the tetrachlorobenzoic acid with thionyl chloride. A six fold molar excess of thionyl chloride is slowly added to the acid. This mixture is heated to reflux and held at this temperature for 1.25 hours. The solution is then cooled and the excess thionyl chloride vacuum distilled off. The solution is further distilled under vacuum to yield the pure tetrachlorobenzoyl chloride in 92-93% yield.

Workup

  1. customThe desired tetrachlorobenzoyl chloride is prepared
  2. temperatureThis mixture is heated
  3. temperatureto reflux
  4. temperatureThe solution is then cooled
  5. distillationthe excess thionyl chloride vacuum distilled off
  6. distillationThe solution is further distilled under vacuum

Sources & evidence

ORD record
ord-593e771099474f27a75f66130eb75eec
Source dataset
uspto-grants-1989_09
Patent number
US04868241

Reaction notes

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