Dimethylformamide → HCID 57091011, Verbindung

HRID 1975632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975632
CN(C)C=O.[O-]CCCC.[K+].[CH3:12][C:13](=[CH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH:21]([CH3:24])[C:20]1([CH3:26])[CH3:25])[C:14](=[O:16])[CH3:15]>C(O)(=O)C>[CH3:12][CH:13]([CH:17]=[CH:18][CH:19]1[CH2:23][CH2:22][CH:21]([CH3:24])[C:20]1([CH3:25])[CH3:26])[C:14](=[O:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 23699084Potassium butoxideHCID 537486543-Methyl-5-(2,2,3-trimethylcyclopentyl)pent-3-en-2-one

Produkt 1

HCID 57091011HCID 57091011, VerbindungAusbeute 20,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a mixture of 100 ml of N,N-dimethylformamide and 13 g (0.18 mole) of powdered potassium butoxide, maintained at 20°-30° C. are added slowly within 1 hour 25 g (0.12 mole) of 3-methyl-5-(2,2,3-trimethyl-cyclopent-1-yl)-pent-3-ene-2-one. The resultant mixture is stirred at ambient temperature for 4 hours (reaction is monitored by GC) and is cooled to 10° C. The reaction mixture is drained out of the reaction flask into a beaker containing 20 ml of glacial acetic acid and 50 ml of ice water which are being stirred by means of a magnetic stirrer. The mixture is stirred for 5-10 minutes and is then transferred to a separatory funnel. This mixture is extracted with three 50 ml portions of toluene. The toluene extracts are combined and washed with three 50 ml portions of 10% sodium bicarbonate solution and one 100 ml portion of saturated sodium chloride solution. The solvent is removed by rotary evaporation and the oil is fractionally distilled to yield 5.2 g of 3-methyl-5-(2,2,3-trimethyl-cyclopent-1-yl)-pent-4-en-2-one (mixtures of isomers).

Aufarbeitung

  1. temperaturemaintained at 20°-30° C.
  2. custom(reaction is monitored by GC)
  3. stirringThe mixture is stirred for 5-10 minutes
  4. customis then transferred to a separatory funnel
  5. extractionThis mixture is extracted with three 50 ml portions of toluene
  6. washwashed with three 50 ml portions of 10% sodium bicarbonate solution and one 100 ml portion of saturated sodium chloride solution
  7. customThe solvent is removed by rotary evaporation
  8. distillationthe oil is fractionally distilled

Quellen und Nachweise

ORD-Eintrag
ord-b02f817d823a4b768953d60ad2d77175
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288701

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