Chlorosulfonic acid → Bicyclo[4.2.0]octa-1,3,5-triene-3-sulfonyl chloride, 8-oxo-

HRID 1861584Notes

Reaction equation

HRID 1861584 reaction equation
[C:1]1(=[O:9])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH2:2]1.[S:10]([Cl:14])(=O)(=[O:12])[OH:11]>C(Cl)(Cl)Cl>[Cl:14][S:10]([C:6]1[CH:7]=[CH:8][C:3]2[CH2:2][C:1](=[O:9])[C:4]=2[CH:5]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 137953Benzocyclobutenone

Product 1

HCID 12067471Bicyclo[4.2.0]octa-1,3,5-triene-3-sulfonyl chloride, 8-oxo-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Benzocyclobutenone (2.36 g, 0.02mol) was added slowly to a strongly stirred chlorosulfuric acid (3 mL) in chloroform (10 mL) solution. After the addition was done, the reaction mixture was stirred for 5 hours. Then the chloroform was evaporated, and the residue was precipitated in water yielding fine pink crystals. m.p. 80° C.; IR (KBr, cm−1): 1762; UV (λmax, methanol) 272 nm.

Workup

  1. additionAfter the addition
  2. customThen the chloroform was evaporated
  3. customthe residue was precipitated in water yielding fine pink crystals

Sources & evidence

ORD record
ord-de38ed9a193744bb8f1285693e2ca4a6
Source dataset
uspto-grants-2003_03
Patent number
US06534250B1

Reaction notes

Loading…