Isopropanol → 7-(2,3-Epoxypropoxy)flavone

HRID 478080

Reaktionsgleichung

Reaktionsgleichung von HRID 478080
[OH-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:24])[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:15]2)=[CH:10][CH:9]=1.C(C1OC1)Cl>O>[O:6]1[CH2:5][CH:3]1[CH2:4][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:24])[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:15]2)=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 52818947-Hydroxyflavone

Produkt 1

HCID 99480817-(2,3-Epoxypropoxy)flavone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 82.2 g (2.06 mol) of sodium hydroxide in 585 ml of water were added 3.7 liters of isopropanol and then 490 g (2.06 mole) of 7-hydroxyflavone. To the above mixture were then added 1645 ml (20.5 mole) of epichlorohydrin and the mixture heated at 70° C. for 2 hours with stirring. The hot reaction mixture was filtered to remove dimeric by-product. The filtrate was concentrated under reduced pressure (water aspirator) at 50°-60° C. The semisolid residue was treated with 4.4 liters of refluxing isopropanol and more of the dimer filtered from the hot mixture. The clear filtrate on cooling yielded a solid. This was filtered, washed with 600 ml of isopropanol and air dried; yield 434.3 g (72%) of a tan-colored product, mp 123°-130° C. (a pure sample melts at 133°-135° C. from i-PrOH). The crude epoxide was used for further reaction.

Aufarbeitung

  1. filtrationThe hot reaction mixture was filtered
  2. customto remove dimeric by-product
  3. concentrationThe filtrate was concentrated under reduced pressure (water aspirator) at 50°-60° C
  4. additionThe semisolid residue was treated with 4.4 liters of refluxing isopropanol and more of the dimer
  5. filtrationfiltered from the hot mixture
  6. temperatureThe clear filtrate on cooling
  7. customyielded a solid
  8. filtrationThis was filtered
  9. washwashed with 600 ml of isopropanol and air
  10. customdried
  11. customThe crude epoxide was used for further reaction

Quellen und Nachweise

ORD-Eintrag
ord-e711f5b358f5408880e3b2f46cab5036
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889941

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