Sodium Chloride → 3-(Chlorosulfonyl)-4-methylbenzoic acid

HRID 873626Notes

Reaction equation

HRID 873626 reaction equation
[Cl-].[Na+].[Cl:3][S:4]([OH:7])(=O)=[O:5].[CH3:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1>>[Cl:3][S:4]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:9]=1[CH3:8])[C:13]([OH:15])=[O:14])(=[O:7])=[O:5]

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 7470P-Toluic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 2418593-(Chlorosulfonyl)-4-methylbenzoic acid

Conditions

Temperature
122 °C

Procedure

Sodium chloride (8 g, 138 mmol) is added to chlorosulfonic acid (30 mL, 451 mmol) and in small portions 4-methyl-benzoic acid (4 g, 29 mmol) is added to the stirred mixture. After complete addition, the reaction is heated at 122° C. for 16 h. The reaction mixture is cooled and poured into ice-water. The organic material is extracted with ethyl acetate. The organic layer is washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and the solvent is removed in vacuo. The residue is used as is in the next step.

Workup

  1. additionis added to the stirred mixture
  2. additionAfter complete addition
  3. temperatureThe reaction mixture is cooled
  4. extractionThe organic material is extracted with ethyl acetate
  5. washThe organic layer is washed with a saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-19dc123a9c9e462186a40a00634c81da
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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