Acetone → (3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one

HRID 654588

Reaktionsgleichung

Reaktionsgleichung von HRID 654588
[CH3:1][C@H:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:3][CH:4]=O.[CH3:12][C:13]([CH3:15])=[O:14]>O>[CH3:1][C@H:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:3]/[CH:4]=[CH:12]/[C:13](=[O:14])[CH3:15]

Komponenten

4

Edukt 2

HCID 180AcetoneHCID 754276-Octenal, 3,7-dimethyl-, (3R)-

Produkt 1

HCID 10965409(3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 25 g (R)-3,7-dimethyl-6-octenal [(R)-citronellal] (chemical purity according to gas chromatography 98.3-98.5%; enantiomeric purity 97-97.6% ee) in 70 ml acetone and 170 ml of water there was added 9.8 g of barium hydroxyde-octahydrate and the mixture was stirred under argon a 68°-69° C. during 4.25 hours. Thereafter, the reaction mixture was cooled to room temperature and extracted two times with 500 ml of n-hexane. The organic phases were combined, washed with 100 ml of water and with 50 ml of 5% aqueous acetic acid, dried over sodium sulfate and concentrated. The so obtained (3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one was 92% chemically pure according to gas chromatography.

Aufarbeitung

  1. extractionextracted two times with 500 ml of n-hexane
  2. washwashed with 100 ml of water and with 50 ml of 5% aqueous acetic acid
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-77bbda3edea04580ba8f7c2f0be1da29
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05132464

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