Potassium Permanganate → HCID 19900799, compound

HRID 1029752Notes

Reaction equation

HRID 1029752 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[N+:7]([CH2:10][S:11]([C:13]1[C:18]2[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:17]=2[CH:16]=[CH:15][CH:14]=1)=[O:12])([O-:9])=[O:8].S(S([O-])=O)([O-])(=O)=[O:27].[Na+].[Na+]>C(O)(=O)C.O>[N+:7]([CH2:10][S:11]([C:13]1[C:18]2[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:17]=2[CH:16]=[CH:15][CH:14]=1)(=[O:27])=[O:12])([O-:9])=[O:8]

Participants

6

Reactant 3

HCID 516875Potassium PermanganateHCID 656671Sodium PyrosulfiteHCID 19900807HCID 19900807, compound

Product 1

HCID 19900799HCID 19900799, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A 3% aqueous solution of potassium permanganate (83 ml, 16.2 mmol) was added to a stirred solution of 4-(nitromethylsulphinyl)dibenzofuran (3.72 g, 13.5 mmol) at 50° C. in acetic acid (100 ml). The reaction mixture was stirred for 1 hour at ambient temperature and then treated with a saturated aqueous solution of sodium metabisulphite until colourless. The reaction mixture was then diluted with water (200 ml). The solid material was removed by filtration, air dried and recrystallised from toluene/cyclohexane to give 4-(nitromethylsulphonyl)dibenzofuran as a white crystalline solid (2.95 g), m.p. 162°-165° C.; NMR (DMSOd6): 6.80 (s,2H) 7.48-8.79 (m,7H); m/e (electron impact): 291 (M+); microanalysis, found: C,53.6; H,3.0; N,4.7%; C13H9NO5S requires: C,53.6; H,3.1; N,4.8%.

Workup

  1. customThe solid material was removed by filtration, air
  2. customdried
  3. customrecrystallised from toluene/cyclohexane

Sources & evidence

ORD record
ord-f1de5f5b953d4ecfa7a13d2aad4ed5de
Source dataset
uspto-grants-1992_04
Patent number
US05102905

Reaction notes

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