Sulfuric Acid → Genistein

HRID 1163262

Reaktionsgleichung

Reaktionsgleichung von HRID 1163262
[C:1](=[O:4])([O-])[O-].[Na+].[Na+].[CH3:7][C:8]([C:10]1[C:15](O)=[CH:14][C:13]([OH:17])=[CH:12][C:11]=1[OH:18])=[O:9].[CH:19]([O:21]S([O-])(=O)=O)=O.[Na+].S(=O)(=O)(O)O>CN(C)C=O>[CH:8]1[C:10]([C:12]2[C:11](=[O:18])[C:10]3[C:8]([OH:9])=[CH:7][C:19]([OH:21])=[CH:14][C:15]=3[O:17][CH:13]=2)=[CH:11][CH:12]=[C:1]([OH:4])[CH:7]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 680732',4',6'-TrihydroxyacetophenoneHCID 23662093Sodium formylsulfate

Produkt 1

HCID 5280961GenisteinAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To 159.8 g of anhydrous sodium carbonate (1.5 mol) in 950 ml of dimethylformamide were added 99.6 g of anhydrous phloroacetophenone (375 mmol) and the resulting yellow suspension was stirred for 3 hours under argon at 25° C., then cooled to 0° C. To this suspension was added the above solution of sodium formylsulfate within 2 minutes and the reaction mixture was stirred for 18 hours at 0° C., heated to 80° C., and held at that temperature during 30 minutes. To the hot mixture were added within 40 minutes 732 ml of sulfuric acid (36%). After gas evolution had ceased, 2.44 l water-dimethylformamide was distilled off at 80° C. and 15 mbar. To the thick suspension were added within 1.5 hours at 70° C. 3.99 l of hot water (50° C.). The white suspension was stirred and cooled to 20° C. overnight, then filtered. The filter cake was washed 3 times with 272 ml of water, then dried at 60° C. at 12 mbar overnight to yield 101.9 g of genistein as a light beige solid. The calculated yield was 95% (purity 93%, w/w, HPLC).

Aufarbeitung

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture was stirred for 18 hours at 0° C.
  3. temperatureheated to 80° C.
  4. waitheld at that temperature during 30 minutes
  5. distillation2.44 l water-dimethylformamide was distilled off at 80° C.
  6. additionTo the thick suspension were added within 1.5 hours at 70° C
  7. custom3.99 l of hot water (50° C.)
  8. stirringThe white suspension was stirred
  9. temperaturecooled to 20° C. overnight
  10. filtrationfiltered
  11. washThe filter cake was washed 3 times with 272 ml of water
  12. customdried at 60° C. at 12 mbar overnight

Quellen und Nachweise

ORD-Eintrag
ord-f91b856f1cad457bad16f127bf9e2555
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820836B2

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