Salicylic Acid → 5-(Chlorosulfonyl)-2-hydroxybenzoic acid

HRID 1930985Notes

Reaction equation

HRID 1930985 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([OH:15])(=[O:14])[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9]>>[Cl:1][S:2]([C:12]1[CH:11]=[CH:10][C:8]([OH:9])=[C:7]([CH:13]=1)[C:6]([OH:15])=[O:14])(=[O:5])=[O:3]

Participants

3

Reactant 2

HCID 338Salicylic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 27772405-(Chlorosulfonyl)-2-hydroxybenzoic acid

Procedure

To 3.26 mol chlorosulfonic acid at 0° C. was added 652 mmol salicylic acid in small portions and the mixture was then allowed to stir at RT for 1 h, then at 50° C. for 1 h, and finally at 70° C. for 1 h. The mixture was then added dropwise to 1000 ml ice-water with stirring and stirring continued for an additional 30 min. The ensuing white crystals were collected by filtration, washed three times with water, and then dried in vacuo at 45° C. for 16 h to yield the title compound. MS (m/e): 236.8 ([{37Cl}M−H]−, 33%), 235.0 ([{37Cl}M−H]−, 100%)

Workup

  1. waitat 50° C. for 1 h
  2. waitfinally at 70° C. for 1 h
  3. stirringwith stirring
  4. stirringstirring
  5. waitcontinued for an additional 30 min
  6. filtrationThe ensuing white crystals were collected by filtration
  7. washwashed three times with water
  8. customdried in vacuo at 45° C. for 16 h

Sources & evidence

ORD record
ord-0b13fa847e7f4da59ddadf9afaf4f6f9
Source dataset
uspto-grants-2012_05
Patent number
US08188139B2

Reaction notes

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