Salicylic Acid → 5-(Chlorosulfonyl)-2-hydroxybenzoic acid
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
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
- waitat 50° C. for 1 h
- waitfinally at 70° C. for 1 h
- stirringwith stirring
- stirringstirring
- wait