Dichloromethane → Methyl 4-(Chlorosulfonyl)benzoate

HRID 401752Notes

Reaction equation

HRID 401752 reaction equation
[Cl:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH2:14](Cl)Cl>S(Cl)(Cl)=O>[Cl:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:14])=[O:10])=[CH:12][CH:13]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 4738388Methyl 4-(Chlorosulfonyl)benzoateYield 96%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

4-Chlorosulphonylbenzoic acid (15 g, 68 mmol, 1 eq) was suspended in thionyl chloride (60 ml) and DCM (60 ml) and the reaction mixture heated at reflux for 2 hours. The solvent was evaporated in vacuo and ice cold MeOH (120 ml) was added to the residue. The reaction was stirred for 10 minutes in an ice bath before the addition of ice cold water (100 ml). The resulting precipitate was collected by filtration to yield the title compound as a white solid (15.3 g, 0.065 mmol, 96%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated in vacuo and ice cold MeOH (120 ml)
  3. additionwas added to the residue
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-13d8770eee364e9fb61c5d175c3e2398
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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