Ethanol → Ethyl alpha-nitro-9H-xanthene-9-acetate

HRID 258187

Reaktionsgleichung

Reaktionsgleichung von HRID 258187
O[CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[N+:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17].[OH-].[K+].C(O)C>O>[N+:16]([CH:19]([CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69379Ethyl nitroacetateHCID 72861Xanthydrol

Produkt 1

HCID 15290758Ethyl alpha-nitro-9H-xanthene-9-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

9-Hydroxyxanthene (9.9 g, 50 mmol) and ethyl nitroacetate (6.1 mL, 55 mol) are mixed and heated at 100° C. (oil bath) for 1.5 hours. After cooling, a waxy mixture is suspended in 40 mL of absolute alcohol and 40 mL of 1.25 M of ethanolic potassium hydroxide solution is added. The solution is stirred for 45 minutes at room temperature and ethanol is stripped off. The remaining solid is suspended in water and extracted with diethyl ether. The aqueous portion is acidified with 85% phosphoric acid to pH 2 to 3 to give a white suspension which is cooled overnight. The precipitate is collected by filtration and dried in a vacuum oven at 50° C. This gives 9.18 g of the title compound as a white solid; mp 89°-91° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. customto give a white suspension which
  4. temperatureis cooled overnight
  5. filtrationThe precipitate is collected by filtration
  6. customdried in a vacuum oven at 50° C

Quellen und Nachweise

ORD-Eintrag
ord-0ae9fb3e0f2140cf8791a86601f25eb2
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264577

Verknüpfte Notizen

Wird geladen…