Benzenesulfonyl chloride → 2,4-Dimethyldiphenylsulfone

HRID 505982

Reaktionsgleichung

Reaktionsgleichung von HRID 505982
CCCCN1C=[N+](C)C=C1.[C:11]1([CH3:18])[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Zn+2]>[CH3:18][C:11]1[CH:16]=[CH:15][C:14]([S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])=[C:13]([CH3:17])[CH:12]=1

Komponenten

5

Edukt 3

HCID 7369Benzenesulfonyl chloride2×HCID 7929M-XyleneHCID 27341621-Butyl-3-methylimidazolium

Produkt 1

HCID 5210842,4-DimethyldiphenylsulfoneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 131725279Zinc(II) bis-triflimideKatalysator

Versuchsvorschrift

Zinc(II) bis-triflimide (0.062 g, 1 mol %) was dissolved in [bmim] [NTf2] (1.0 g) in a round-bottomed flask equipped with a magnetic stirrer and reflux condenser and m-xylene (2.12 g, 20 mmol) and benzene sulfonyl chloride (1.76 g, 10 mmol) were added. The mixture was heated under reflux for 18 hours and was analysed by gas chromatographic analysis as in previous examples. All the benzene sulfonyl chloride had reacted and mostly 2,4-dimethyldiphenylsulfone had formed (yield=99%, 20:1 isomer ratio {by NMR}). The major product is shown below, the structure of the minor isomer is not known but is believed to be the 2,6-dimethyl isomer.

Aufarbeitung

  1. customequipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 18 hours

Quellen und Nachweise

ORD-Eintrag
ord-2dee0ecbec004775a240ba780a38d605
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781625B2

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