3-Chloro-4-hydroxybenzoic acid → 3-Chloro-5-(chlorosulfonyl)-4-hydroxybenzoic acid

HRID 1889689Notes

Reaction equation

HRID 1889689 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[OH:16])[C:10]([OH:12])=[O:11]>>[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([S:2]([Cl:1])(=[O:5])=[O:3])[C:15]=1[OH:16])[C:10]([OH:12])=[O:11]

Participants

3

Reactant 2

HCID 198603-Chloro-4-hydroxybenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 545935123-Chloro-5-(chlorosulfonyl)-4-hydroxybenzoic acidYield 74.2%

Conditions

Temperature
65 °C

Procedure

To a flask charged with chlorosulfonic acid (13.9 mL, 209.0 mmol) was added 3-chloro-4-hydroxybenzoic acid (6.0 g, 34.8 mmol) portionwise over ten minutes. The mixture was then heated for 2 h at 65° C. under a nitrogen atmosphere. After cooling the mixture to room temperature, the reaction mixture was carefully poured over crushed ice with vigorous stirring, and extracted with Et2O until no further product remained in the aqueous layer. The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 3-chloro-5-(chlorosulfonyl)-4-hydroxy-benzoic acid as a white solid (7.0 g, 74%) which was used without further purification.

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. additionthe reaction mixture was carefully poured
  3. customover crushed ice with vigorous stirring
  4. extractionextracted with Et2O until no further product
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eee0062f1bd8493f915096a8259e9162
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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