4-Methoxyphenol → HCID 15540784, Verbindung

HRID 1600852

Reaktionsgleichung

Reaktionsgleichung von HRID 1600852
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.F[C:11]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH3:32][O:33][C:34]1[CH:40]=[CH:39][C:37]([O-:38])=[CH:36][CH:35]=1.[Na+:41]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O-:9])=[CH:5][CH:4]=1.[Na+:41].[CH3:32][O:33][C:34]1[CH:40]=[CH:39][C:37]([O:38][C:11]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][C:26]4[O:29][CH2:30][O:31][C:25]=4[CH:24]=3)[C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:36][CH:35]=1

Komponenten

6

Edukt 3

HCID 90154-MethoxyphenolHCID 15540783HCID 15540783, VerbindungHCID 23679016Sodium 4-methoxyphenolate

Produkt 2

HCID 15540784HCID 15540784, VerbindungHCID 23679016Sodium 4-methoxyphenolate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium 4-methoxyphenoxide was prepared as described in part A using 4-methoxyphenol (156 mg, 1.25 mmol) and was dried in vacuo. A solution of ethyl 2-fluoro-6-[3,4-(methylenedioxy)phenoxy]benzoate (304 mg, 1.0 mmol) in DMSO was added to the sodium 4-methoxyphenoxide at 25° C. and the mixture was stirred until all the solid had dissolved (approximately 20 min.). Stirring was continued at 25° C. for an additional 24 hr. The reaction mixture was then warmed to 60° C. and stirred for 2 hr., then stirred for 4 hr. at 80° C. At this time all of the ethyl 2-fluoro-6-[3,4-(methylenedioxy)phenoxy]benzoate had been consumed, as judged by thin layer chromatography (TLC). The reaction was cooled to 25° C., diluted with water (10 ml) and extracted with EtOAc (3×10 ml). The organic extract was washed with water (2×7 ml) and brine (7 ml), dried (MgSO4) and concentrated to give a light yellow oil. The crude product was purified by flash chromatography (SiO2, 50% CH2Cl2 /hexane--CH2Cl2) giving 195 mg of ethyl 2-(4-methoxyphenoxy)-6-[3,4-(methylenedioxy)phenoxy]benzoate. (47% yield, m.p. 84.5-85° C.).

Aufarbeitung

  1. customwas dried in vacuo
  2. dissolutionhad dissolved (approximately 20 min.)
  3. stirringStirring
  4. stirringstirred for 2 hr
  5. stirring, then stirred for 4 hr
  6. customat 80° C
  7. customAt this time all of the ethyl 2-fluoro-6-[3,4-(methylenedioxy)phenoxy]benzoate had been consumed
  8. temperatureThe reaction was cooled to 25° C.
  9. additiondiluted with water (10 ml)
  10. extractionextracted with EtOAc (3×10 ml)
  11. extractionThe organic extract
  12. washwas washed with water (2×7 ml) and brine (7 ml)
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated
  15. customto give a light yellow oil
  16. customThe crude product was purified by flash chromatography (SiO2, 50% CH2Cl2 /hexane--CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-4925a10d8a8c4b799fbea34a41c7a8f6
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977117

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