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

HRID 1169172

Reaktionsgleichung

Reaktionsgleichung von HRID 1169172
[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-46f57410df214d7299eca4fe3ee43426
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627763B2

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