Salicylic Acid → 3,5-Bis(chlorosulfonyl)-2-hydroxybenzoic acid

HRID 614815Notes

Reaction equation

HRID 614815 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Cl:11][S:12]([OH:15])(=O)=[O:13]>O>[Cl:11][S:12]([C:5]1[CH:6]=[C:7]([S:12]([Cl:11])(=[O:15])=[O:13])[CH:8]=[C:2]([C:1]([OH:10])=[O:9])[C:3]=1[OH:4])(=[O:15])=[O:13]

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 130269203,5-Bis(chlorosulfonyl)-2-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Salicylic acid (10 g) was added to chlorosulphonic acid (60 ml) during 5 minutes. The mixture was then heated at 130°-140° C. for 90 minutes. After cooling, the mixture was cooled and then added dropwise to an excess of a mixture of ice and water, keeping the temperature below 0° C. The precipitated solid was extracted with dichloromethane, and the organic extract was dried over sodium sulphate, and concentrated in vacuo to a small volume and treated with petroleum ether (b.p. 40°-60° C.). The precipitate was filtered off and recrystallized from a large volume of toluene to give 3,5-bis(chlorosulphonyl)salicylic acid (9.95 g), m.p. 185°-187° C.

Workup

  1. temperatureThe mixture was then heated at 130°-140° C. for 90 minutes
  2. temperatureAfter cooling
  3. temperaturethe mixture was cooled
  4. additionadded dropwise to an
  5. customthe temperature below 0° C
  6. extractionThe precipitated solid was extracted with dichloromethane
  7. extractionthe organic extract
  8. dry with materialwas dried over sodium sulphate
  9. concentrationconcentrated in vacuo to a small volume
  10. additiontreated with petroleum ether (b.p. 40°-60° C.)
  11. filtrationThe precipitate was filtered off
  12. customrecrystallized from a large volume of toluene

Sources & evidence

ORD record
ord-ca5060e296fd49db98476f5a6bfa23f9
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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