3,5-Dichlorobenzoic acid → 3,5-Dichlorobenzoyl chloride

HRID 2121276Notes

Reaction equation

HRID 2121276 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:9](O)=[O:10]>N1C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:9]([Cl:3])=[O:10]

Participants

4

Reactant 2

HCID 58113,5-Dichlorobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 761913,5-Dichlorobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

49.4 g of thionyl chloride and 0.21 g of pyridine were added to 20 g of 3,5-dichlorobenzoic acid and the mixture was refluxed for 20 hours. Excessive thionyl chloride was removed by distillation. Dry hexane was added to the residue and an insoluble matter was filtered out of the resulting solution and hexane was removed under reduced pressure. The remaining solution was crystallized. 3,5-Dichlorobenzoyl chloride was obtained quantitatively.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. customExcessive thionyl chloride was removed by distillation
  3. additionDry hexane was added to the residue
  4. filtrationan insoluble matter was filtered out of the resulting solution and hexane
  5. customwas removed under reduced pressure
  6. customThe remaining solution was crystallized

Sources & evidence

ORD record
ord-9abcd42089324f9b91a798351f5506c6
Source dataset
uspto-grants-2004_02
Patent number
USRE038435E1

Reaction notes

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