Ethanol → 1,3-Dihydro-2H-2-benzothiophene-2,2-dione

HRID 248099Notes

Reaction equation

HRID 248099 reaction equation
[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].[CH2:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11]S1.C(O)C>O>[CH2:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH2:11][S:1]1(=[O:6])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 137608Benzo(c)thiophene, 1,3-dihydro-HCID 10313463Potassium peroxymonosulphate

Product 1

HCID 3136751,3-Dihydro-2H-2-benzothiophene-2,2-dioneYield 59.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Potassium peroxymonosulphate (110 g) was added portionwise to a mixture of 1,3-dihydrobenzo[c]thiophene (23 g; J. Amer. Chem. Soc., 81, 4266), ethanol (400 ml) and water (300 ml) and the mixture was stirred at ambient temperature for 18 hours. Water (400 ml) was added and the mixture was extracted with chloroform (3×100 ml). The combined organic extracts were washed with water, dried (MgSO4) and evaporated. The residue was recrystallised from ethyl acetate to give 1,3-dihydrobenzo[c]thiophene-2,2-dioxide (17 g).

Workup

  1. extractionthe mixture was extracted with chloroform (3×100 ml)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-9b0b1b89bac74aa58688801143ad6735
Source dataset
uspto-grants-1993_05
Patent number
US05208259

Reaction notes

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