Beta-citronellol, (S)- → Pulegone, (-)-

HRID 2051370

Reaktionsgleichung

Reaktionsgleichung von HRID 2051370
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C:13](=[CH:15][CH2:16][CH2:17][C@@H:18]([CH2:20][CH2:21][OH:22])[CH3:19])[CH3:14]>C(Cl)Cl>[CH3:19][C@@H:18]1[CH2:20][C:21](=[O:22])[C:15](=[C:13]([CH3:14])[CH3:12])[CH2:16][CH2:17]1

Komponenten

4

Edukt 2

HCID 7793Beta-citronellol, (S)-HCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 638012Pulegone, (-)-Ausbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10 l of CH2Cl2 and 1704 g (7.89M) of pyridinium chlorochromate were introduced in a four neck reaction vessel equipped with a mechanical stirrer, a thermometer, a condenser and an inlet tube for nitrogen. To this mixture and under nitrogen, 400 g (2.56M) of (-)-(S)-β-citronellol were added while the temperature was kept at 15°-20°. Stirring was then carried on for 60 h at room temperature. After filtration, the mixture was extracted with CH2Cl2 and the combined organic extracts were washed with 15% HCl, saturated NaHCO3, then with water until neutrality. Evaporation and distillation on residue at 7.8 mmHg gave 206.9 g of (-)-pulegone and (-)-isopulegone (40:60) (yield 37%). B.p. 62°/7.8 mmHg).

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. customwas kept at 15°-20°
  3. customwas then carried on for 60 h at room temperature
  4. filtrationAfter filtration
  5. extractionthe mixture was extracted with CH2Cl2
  6. washthe combined organic extracts were washed with 15% HCl, saturated NaHCO3
  7. customEvaporation and distillation on residue at 7.8 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-4758270304114f47a4838cad26304fcb
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05017711

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