Sodium Iodide → 1,1'-Dithiobis(2,4,6-trimethylbenzene) dimesityl disulfide

HRID 2184163

Reaktionsgleichung

Reaktionsgleichung von HRID 2184163
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10](Cl)(=O)=O.[Na+].[I-].FCC(O[C:21](=O)[CH2:22]F)=O>CC(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10][S:10][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:21]=1[CH3:22]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 130462-Mesitylenesulfonyl chlorideHCID 67886Acetic acid, 2-fluoro-, 1,1'-anhydride

Produkt 1

HCID 3456131,1'-Dithiobis(2,4,6-trimethylbenzene) dimesityl disulfide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2,4,6-trimethylphenylsulfonyl chloride (500 mg, 2.3 mmol) was dissolved in acetone (60 mL), and then NaI (3.4 g, 23 mmol) and fluoroacetic anhydride (1.45 mL, 6.9 mmol) were added and the mixture was stirred at room temperature for one hour. The reaction solution was concentrated, water was added, extraction was performed with ether and the organic layer was further washed with aqueous sodium thiosulfate, water and saturated saline. After drying over magnesium sulfate and vacuum concentration, the residue was purified with a silica gel column (hexane) to obtain 2,4,6-trimethylphenyldisulfide as a light yellow crystalline compound (231 mg, 0.76 mmol, 67% yield). The NMR and mass spectral data for the obtained compound were as follows:

Aufarbeitung

  1. concentrationThe reaction solution was concentrated
  2. additionwater was added
  3. extractionextraction
  4. washthe organic layer was further washed with aqueous sodium thiosulfate, water and saturated saline
  5. dry with materialAfter drying over magnesium sulfate and vacuum concentration
  6. customthe residue was purified with a silica gel column (hexane)

Quellen und Nachweise

ORD-Eintrag
ord-66600d1abbe64ed2958ff894b380c2be
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900307B1

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