4-Hydroxybenzenesulfonic acid → 4-(Chlorosulfonyl)phenyl acetate

HRID 1686257Notes

Reaction equation

HRID 1686257 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:15])=O.[C:18]([O:21]C(=O)C)(=O)[CH3:19]>C(O)(=O)C.CN(C=O)C>[C:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([Cl:15])(=[O:10])=[O:11])=[CH:6][CH:7]=1)(=[O:21])[CH3:19]

Participants

6

Reactant 3

HCID 47654-Hydroxybenzenesulfonic acidHCID 7918Acetic AnhydrideHCID 65578Oxalyl chloride

Product 1

HCID 129257104-(Chlorosulfonyl)phenyl acetateYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 176Acetic AcidSolvent

Procedure

6.285 g (36.08 mmol) of 4-hydroxybenzenesulfonic acid was dissolved in a mixture of 30 mL of acetic anhydride and 15 mL of acetic acid and refluxed for 6 hours. The volatiles were evaporated and placed under high vacuum overnight. The resulting crude product was dissolved in 100 mL of DCM and treated with 4.72 mL of oxalyl chloride (54.12 mmol) and 139 μL of DMF (1.804 mmol) at 0° C. Stirring was continued until gas evolution ceased then the reaction was concentrated and re-dissolved in EtOAc. The organic layer was washed twice with 2 N H2SO4, and dried with brine and MgSO4. concentration gave 7.067 g of 4-(chlorosulfonyl)phenyl acetate as a dark thick oil that eventually solidified (83% yield over two steps).

Workup

  1. temperaturerefluxed for 6 hours
  2. customThe volatiles were evaporated
  3. customplaced under high vacuum overnight
  4. dissolutionThe resulting crude product was dissolved in 100 mL of DCM
  5. concentrationthe reaction was concentrated
  6. dissolutionre-dissolved in EtOAc
  7. washThe organic layer was washed twice with 2 N H2SO4
  8. dry with materialdried with brine and MgSO4
  9. concentrationconcentration

Sources & evidence

ORD record
ord-4902fea6494a4439b82f7388e8c05775
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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