Sulfuric Acid → Benzo(b)thiophene-3(2H)-one 1,1-dioxide

HRID 326966Notes

Reaction equation

HRID 326966 reaction equation
[O:1]=[C:2]1[CH:6](C(OCC)=O)S[C:4]2[CH:12]=[CH:13][CH:14]=[CH:15][C:3]1=2.[OH:16][S:17]([OH:20])(=O)=O>>[O:1]=[C:2]1[CH2:6][S:17](=[O:20])(=[O:16])[C:4]2[CH:12]=[CH:13][CH:14]=[CH:15][C:3]1=2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 19734103HCID 19734103, compound

Product 1

HCID 70780Benzo(b)thiophene-3(2H)-one 1,1-dioxideYield 90%

Procedure

A suspension of Compound X (130.0 g, 0.51 mol) in 350 ml of 10% aqueous H2SO4 was heated at reflux for 6 h (until gas evolution ceased). The reaction mixture was cooled and a white solid precipitated, which was collected by filtration and washed in cold water (30 ml). The product was recrystallized from ethanol to give 83.8 g (90%) of Compound Y as a white crystalline solid:melting point 133°-134° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h (until gas evolution ceased)
  3. temperatureThe reaction mixture was cooled
  4. customa white solid precipitated
  5. filtrationwhich was collected by filtration
  6. washwashed in cold water (30 ml)
  7. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-0a374df4b10c4ad3bea183ddff4b56d8
Source dataset
uspto-grants-1993_12
Patent number
US05272032

Reaction notes

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