4-Hydroxybenzoic Acid → 3-(Chlorosulfonyl)-4-hydroxybenzoic acid

HRID 464754Notes

Reaction equation

HRID 464754 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

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 126948493-(Chlorosulfonyl)-4-hydroxybenzoic acidYield 69%

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

  1. additionAfter 18 hours the reaction mixture was poured in a thin stream
  2. filtrationThe product was filtered
  3. dissolutionthe precipitate dissolved in ethyl acetate
  4. washThe solution was then washed with brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c4654e3d0f324823875904f94edba0ed
Source dataset
uspto-grants-1985_10
Patent number
US04548951

Reaction notes

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