Methyl p-toluenesulfonate → Triphenylsulfonium p-toluenesulfonate

HRID 1168008

Reaktionsgleichung

Reaktionsgleichung von HRID 1168008
[I-].[C:2]1([S+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([CH3:32])[CH:26]=[CH:25][C:24]([S:27]([O:30]C)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(#N)C>[C:21]1([CH3:32])[CH:22]=[CH:23][C:24]([S:27]([O-:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1.[C:15]1([S+:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

4

Edukt 2

HCID 6645Methyl p-toluenesulfonateHCID 21881071Triphenylsulfonium iodide

Produkt 1

HCID 21872467Triphenylsulfonium p-toluenesulfonateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Acetonitrile (500 ml) was added to triphenylsulfonium iodide (390.3 g; 1.0 mol) and methyl p-toluenesulfonate (223.5 g; 1.2 mol). The resultant mixture was heated at 82° C.-85° C. and refluxed for 5 hours while being stirred. The reaction mixture was cooled, and acetonitrile was removed through distillation under reduced pressure. The thus-obtained pale-yellow solid was washed with methylene chloride, and dried under vacuum, to thereby yield 369.4 g of triphenylsulfonium p-toluenesulfonate (yield: 85%).

Aufarbeitung

  1. temperaturerefluxed for 5 hours
  2. temperatureThe reaction mixture was cooled
  3. customacetonitrile was removed through distillation under reduced pressure
  4. washThe thus-obtained pale-yellow solid was washed with methylene chloride
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-aabcb37103414a93a0522f2b2909ba80
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620957B1

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