Citronellol → 4-Oxo-decanoic Acid 3,7-dimethyl-oct-6-enyl Ester

HRID 1018160

Reaktionsgleichung

Reaktionsgleichung von HRID 1018160
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:14][C:15](=[CH:17][CH2:18][CH2:19][CH:20]([CH2:22][CH2:23]O)[CH3:21])[CH3:16]>C1CCCCC1.CCOCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:21][CH:20]([CH2:19][CH2:18][CH:17]=[C:15]([CH3:16])[CH3:14])[CH2:22][CH2:23][O:6][C:5](=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 2

HCID 8842CitronellolHCID 5386474-Oxo capric acid

Produkt 1

HCID 538305424-Oxo-decanoic Acid 3,7-dimethyl-oct-6-enyl EsterAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

A solution of 20.0 g 4-oxo-1-decanoic acid (Synthesis, 1987, 408), 16.8 g citronellol extra and 0.5 g p-toluene-sulfonic acid in 150 ml of cyclohexane was refluxed in a flask equipped with a Dean-Stark trap for 3 hours. Then the reaction mixture was cooled, diluted with ether, washed with saturated NaHCO3 and water. The organic phase was dried, filtered and evaporated to dryness. The resulting oil was purified by chromatography to yield 31.7 g of a yellow oil.

Aufarbeitung

  1. customequipped with a Dean-Stark trap for 3 hours
  2. temperatureThen the reaction mixture was cooled
  3. washwashed with saturated NaHCO3 and water
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting oil was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-11630feaa8de4c1b838b6cbecb81d087
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479682B1

Verknüpfte Notizen

Wird geladen…