Dimethyl Sulfoxide → Diphenoxymethane

HRID 358421

반응식

HRID 358421 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 78183Diphenoxymethane

시약·촉매·용매 1

HCID 23978Copper촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-795e17da526d478bbf905f1581d8d682
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04468247

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