Chlorosulfonic acid → 4-(Chlorosulfonyl)benzoic acid

HRID 263658Notes

Reaction equation

HRID 263658 reaction equation
[S:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(O)(=[O:3])=[O:2].[K].[Cl:15]S(O)(=O)=O>>[Cl:15][S:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:3])=[O:2]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 162119825399-63-3

Product 1

HCID 823854-(Chlorosulfonyl)benzoic acid

Conditions

Temperature
100 °C

Procedure

4-Chlorosulfonylbenzoic acid is prepared by procedures described in (J. Chem. Soc., Vol. 121, 2022-26, 1922). A 250 mL flask equipped with condenser, CaCl2 drying tube and magnetic stirrer is charged with 35.1 g (0.146 mol) of potassium 4-sulfobenzoic acid and 50 mL of chlorosulfonic acid. The flask is placed in an oil bath and warmed to 100° C. After 1 hour at temperature, the reaction mixture is homogeneous. The reaction mixture is cooled and poured onto 300 g of crushed ice. The white precipitate is collected by filtration and washed 3 times with 100 mL portions of cold water. After air drying the solid is placed in a vacuum oven at 65° C. to yield 26.7 g of 4-chlorosulfonyl benzoic acid.

Workup

  1. custom4-Chlorosulfonylbenzoic acid is prepared by procedures
  2. customA 250 mL flask equipped with condenser, CaCl2 drying tube and magnetic stirrer
  3. customThe flask is placed in an oil bath
  4. temperatureThe reaction mixture is cooled
  5. filtrationThe white precipitate is collected by filtration
  6. washwashed 3 times with 100 mL portions of cold water
  7. customAfter air drying the solid
  8. customis placed in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-ec4d4fff87ca45b3a9342fca35014bfe
Source dataset
uspto-grants-1997_07
Patent number
US05644017

Reaction notes

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