4-Chlorobenzoic Acid → 4-Chloro-3-(chlorosulphonyl)benzoic acid

HRID 1992065Notes

Reaction equation

HRID 1992065 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][S:12](O)(=[O:14])=[O:13]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:12]([Cl:11])(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 63184-Chlorobenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 756134-Chloro-3-(chlorosulphonyl)benzoic acid

Procedure

At 5-10° C., to stirred chlorosulfonic acid (200 mL) was added 4-chlorobenzoic acid (78 g, 0.5 mol). The reaction mixture was then brought up to 150˜160° C. for 5 hours. After being cooled down to room temperature, the reaction mixture was slowly poured onto a large amount of ice and extracted with ether. The combined organic extracts were washed with ice water and dried over anhydrous magnesium sulfate. Evaporation of solvents afforded 4-chloro-3-(chlorosulfonyl)benzoic acid as a solid (76 g), which was directly used in the next steps.

Workup

  1. additionthe reaction mixture was slowly poured onto a large amount of ice
  2. extractionextracted with ether
  3. washThe combined organic extracts were washed with ice water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of solvents

Sources & evidence

ORD record
ord-0ecbc521b4944894ae27a9f0f030af3a
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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