Ethanol → HCID 10899886, Verbindung

HRID 329473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 329473
[CH3:1][O:2][C:3]([CH3:9])([CH3:8])[CH2:4][CH2:5][CH:6]=O.C(OCC)(=O)[CH2:11][C:12]([CH3:14])=O.N1CCCC[CH2:20]1.[CH2:25]([OH:27])[CH3:26]>>[CH3:1][O:2][C:3]([CH3:9])([CH3:8])[CH2:4][CH2:5][CH:6]1[CH2:14][C:12]([CH3:11])=[CH:20][C:25](=[O:27])[CH2:26]1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 8082Piperidine2×HCID 8868Ethyl AcetoacetateHCID 118294744-Methoxy-4-methylpentanal

Produkt 1

HCID 10899886HCID 10899886, Verbindung

Versuchsvorschrift

To a stirred mixture of 4-methoxy-4-methylpentanal (60 g, 0.46 mol) and ethyl acetoacetate (156 g, 1.2 mol) at 5° C. was added a 21% solution of piperidine in ethanol (4.1 mL). Further additions (4×18 mL) of the piperidine solution were made at about 24 hour intervals. The mixture was heated at reflux for 7 hours and concentrated to about 200 mL volume. Methanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added and the resulting mixture was heated at reflux 16 hours. Workup gave 3-(3-methoxy-3-methylbut-1-yl)-5-methylcyclohex-5-en-1-one bp0.1 135°-140° C. (69.2 g); NMR(CDCl3)δ1.2(s,6H), 0.9-1.6(m,5H), 1.9(s,3H), 5.9(brs,1H); IR(neat) 2975, 2930, 1675, 1640, 1380, 1080 cm-1 ; MS(m/e) 43, 73, 81, 109, 122, 163, 196.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 hours
  3. concentrationconcentrated to about 200 mL volume
  4. additionMethanol (420 mL), water (420 mL) and sodium hydroxide (24 g) were added
  5. temperaturethe resulting mixture was heated
  6. temperatureat reflux 16 hours

Quellen und Nachweise

ORD-Eintrag
ord-b05b65604c98438ab94b09ec1a6e2082
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04891447

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