4-Hydroxybenzoic Acid → 3-(Chlorosulfonyl)-4-hydroxybenzoic acid
Reaction equation
[OH: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:11][S:12]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[OH:1])[C:6]([OH:8])=[O:7])(=[O:14])=[O:13]Participants
3
Procedure
55 g of p-Hydroxybenzoic acid (I) (Aldrich) was added in small portions to 545 g of chlorosulfonic acid (Aldrich) while stirring at room temperature. After 18 hours the reaction mixture was poured in a thin stream upon crushed ice (5 liters). The product was filtered and the precipitate dissolved in ethyl acetate. The solution was then washed with brine, dried with magnesium sulfate, filtered and evaporated to yield 65 g of 3-chlorosulfonyl-4-hydroxybenzoic acid (II), m.p. 181°-182° C.
Workup
- additionAfter 18 hours the reaction mixture was poured in a thin stream
- filtrationThe product was filtered
- dissolutionthe precipitate dissolved in ethyl acetate
- washThe solution was then washed with brine
- dry with materialdried with magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-c4654e3d0f324823875904f94edba0ed
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04548951
Reaction notes
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