Ethyl Acetate → HCID 7172095, Verbindung

HRID 1844606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844606
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[C:9]([C:13]1[CH:14]=[CH:15][C:16]([OH:21])=[C:17]([CH:20]=1)[CH:18]=[O:19])([CH3:12])([CH3:11])[CH3:10].C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C(#N)C>[C:9]([C:13]1[CH:14]=[C:15]([N+:7]([O-:8])=[O:6])[C:16]([OH:21])=[C:17]([CH:20]=1)[CH:18]=[O:19])([CH3:12])([CH3:10])[CH3:11]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 14750905-tert-ButylsalicylaldehydeHCID 11073463Nitronium tetrafluoroborate

Produkt 1

HCID 7172095HCID 7172095, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

At −30° C. 4.84 g nitroniumtetrafluoroborate are added to a solution of 5.00 g 5-tert-butyl-2-hydroxy-benzaldehyde in 200 ml acetonitrile. The solution is heated to −15° C. within 1 h and then combined with ethyl acetate and saturated aqueous NaHCO3 solution. The resulting mixture is extracted with ethyl acetate, and the combined extracts are washed with saturated aqueous saline solution, dried (MgSO4) and evaporated down. The residue is taken up in 2 ml of water and 40 ml concentrated acetic acid, and the resulting mixture is refluxed for 2 h. The cooled solution is poured into ice-cold water, and the precipitate formed is filtered off and dissolved in ethyl acetate. The organic solution is dried (MgSO4) and evaporated down. The oil remaining rapidly solidifies.

Aufarbeitung

  1. customAt −30° C
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washthe combined extracts are washed with saturated aqueous saline solution
  4. dry with materialdried (MgSO4)
  5. customevaporated down
  6. temperature40 ml concentrated acetic acid, and the resulting mixture is refluxed for 2 h
  7. additionThe cooled solution is poured into ice-cold water
  8. customthe precipitate formed
  9. filtrationis filtered off
  10. dissolutiondissolved in ethyl acetate
  11. dry with materialThe organic solution is dried (MgSO4)
  12. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-7fad12f122484f8f96a1237ed039aa89
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946438B2

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