Triethylamine → 2-Acetyl-1,3-cyclohexanedione

HRID 393907

Reaktionsgleichung

Reaktionsgleichung von HRID 393907
[C:1](OC1C=CC([N+]([O-])=O)=CC=1)(=[O:3])[CH3:2].[C:14]1(=[O:21])[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[CH2:15]1.C(N(CC)CC)C>CC(C)(O)C#N.C(#N)C>[C:1]([CH:15]1[C:16](=[O:20])[CH2:17][CH2:18][CH2:19][C:14]1=[O:21])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 132434-Nitrophenyl Acetate

Produkt 1

HCID 1381042-Acetyl-1,3-cyclohexanedioneAusbeute 518,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6406Acetone CyanohydrinKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A 200-mL 2-necked round bottom flask was fitted with thermometer, reflux condenser, magnetic stirrer, and nitrogen bypass. The flask was charged with 4.53 g (25 mmol) of 4-nitrophenyl acetate, 2.94 g (26.25 mmol) of 1,3-cyclohexanedione, 5.69 g (56.25 mmol) of triethylamine, 0.22 g (2.5 mmol) of acetone cyanohydrin, and 60 mL of acetonitrile. The mixture was heated to reflux with stirring for 3 hr. The mixture was allowed to cool to room temperature and volatiles were removed under reduced pressure to give 20.0 g of red oil. Chromatographic separation on silica gel afforded the title product. 1H NMR (CDCl3): δ 1.99 (m, 2), 2.52 (m, 2), 2.62 (s, 3), 2.68 (m, 2).

Aufarbeitung

  1. customA 200-mL 2-necked round bottom flask was fitted with thermometer
  2. temperaturereflux condenser, magnetic stirrer
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customvolatiles were removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4f62be12ed224d7fb63ccba478486fa4
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809206B2

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