Dimethyl Sulfoxide → Diphenoxymethane

HRID 358421

Reaktionsgleichung

Reaktionsgleichung von HRID 358421
CO[C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].FC(F)(F)[C:15]1[CH:20]=[CH:19][C:18](Cl)=[C:17](Cl)[CH:16]=1.CS(C)=[O:27]>[Cu]>[O:27]([CH2:10][O:9][C:5]1[CH:4]=[CH:3][CH:8]=[CH:7][CH:6]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 90251,3-DimethoxybenzeneHCID 94813,4-DichlorobenzotrifluorideHCID 24758Sodium hydride

Produkt 1

HCID 78183Diphenoxymethane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

To m-methoxyanisole (100 g) in DMSO (350 ml) was added 39 g sodium hydride (50%) in portions. The solution was stirred at room temperature under nitrogen overnight. 4-Trifluoromethyl-1,2-dichlorobenzene (173.2 g) was added to the solution in one portion, followed by copper powder (2 spatulas) and 18-crown ether (i,4,7,10,13,16-hexaoxacyclooctadecane, 2 g). The slurry was kept 152°-170° under nitrogen for 24 hours, then added to ice (1.5 l). The mixture was allowed to stand until the ice melted, then filtered. The solid which was collected was dissolved in methylene chloride (1.5 l) and filtered. The aqueous filtrate was extracted with methylene chloride (500 ml) and the methylene chloride phase was washed with water, dried (MgSO4), filtered and stripped to yield a dark oil. The other methylene chloride solution (1.5 l) was washed with water, dried (MgSO4), filtered and stripped to yield an oil. Both oil fractions were treated with petroleum ether and filtered. The filtrates were combined and stripped to yield the phenoxy methoxybenzene product, 244 g.

Aufarbeitung

  1. waitThe slurry was kept 152°-170° under nitrogen for 24 hours
  2. filtrationfiltered
  3. customThe solid which was collected
  4. dissolutionwas dissolved in methylene chloride (1.5 l)
  5. filtrationfiltered
  6. extractionThe aqueous filtrate was extracted with methylene chloride (500 ml)
  7. washthe methylene chloride phase was washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customto yield a dark oil
  11. washThe other methylene chloride solution (1.5 l) was washed with water
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. customto yield an oil
  15. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-795e17da526d478bbf905f1581d8d682
Quelldatensatz
uspto-grants-1984_08
Patentnummer
US04468247

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