(4S)-4,8-dimethyl-7-nonen-2-ol → (4S)-4,8-dimethyl-7-nonen-2-one

HRID 1835060

Reaktionsgleichung

Reaktionsgleichung von HRID 1835060
[CH3:1][C@@H:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:3][CH:4]([OH:6])[CH3:5].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S([O-])(O)=O.[Na+]>[Cr+6].CC(C)=O>[CH3:1][C@@H:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12])[CH2:3][C:4](=[O:6])[CH3:5]

Komponenten

6

Edukt 3

HCID 12084285(4S)-4,8-dimethyl-7-nonen-2-olHCID 23665763Sodium BisulfiteHCID 131709961Jones' reagent

Produkt 1

HCID 11446560(4S)-4,8-dimethyl-7-nonen-2-oneAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 29131Chromium(6+)KatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

Acetone (2,000 ml) and the (4S)-4,8-dimethyl-7-nonen-2-ol (240 g) synthesized in Reference Example 1 were placed in a 5-liter, 4-necked flask equipped with a dropping funnel, thermometer, condenser and stirrer. Jones reagent (prepared from water (520 ml), conc. sulfuric acid (165 g) and chromium trioxide (112 g)) placed in the dropping funnel was dropped in over the course of 4 hours while cooling with ice. After the dropwise addition, the mixture was stirred for 2 hours. The sodium hydrogen sulfite was added little by little until the orange color of chromium (VI) disappeared. The liquid was then separated and the bottom layer was extracted with petroleum ether (1,000 ml). Since the liquid was again separated into two layers when the extract was combined with the top layer, that bottom layer was added to the previous bottom layer and additionally extracted three times with 500 ml of petroleum ether. After combining the extracts and washing with a saturated brine, a saturated aqueous sodium hydrogencarbonate solution and again with a saturated brine, the solvent was distilled off and the resulting concentrated oil was distilled with a Widmer distiller to obtain 194 g of (4S)-4,8-dimethyl-7-nonen-2-one: (4S)-(14) (b.p.: 63° C./133 Pa (1.0 torr)).

Aufarbeitung

  1. customequipped with a dropping funnel
  2. additionwas dropped in over the course of 4 hours
  3. temperaturewhile cooling with ice
  4. additionAfter the dropwise addition
  5. customThe liquid was then separated
  6. extractionthe bottom layer was extracted with petroleum ether (1,000 ml)
  7. customSince the liquid was again separated into two layers when the extract
  8. additionwas added to the previous bottom layer
  9. extractionadditionally extracted three times with 500 ml of petroleum ether
  10. washwashing with a saturated brine
  11. distillationa saturated aqueous sodium hydrogencarbonate solution and again with a saturated brine, the solvent was distilled off
  12. concentrationthe resulting concentrated oil
  13. distillationwas distilled with a Widmer distiller

Quellen und Nachweise

ORD-Eintrag
ord-096ebe26377d45d1aa903ecda59ffae3
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06770618B2

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