Hydrochloric Acid → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

HRID 48546

Reaktionsgleichung

Reaktionsgleichung von HRID 48546
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4][OH:5].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].FC1C=CC=CC=1C=O.Cl>C1CCCCC1.CCCCCC>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH:4]=[O:5]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 67970o-FluorobenzaldehydeHCID 445070Farnesol

Produkt 1

HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienalAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol (1.3 g, 6.0 mmol) was dissolved in cyclohexane (4.5 mL), added with aluminum isopropoxide (123 mg, 0.1 eq, 0.6 mmol) and 2-fluorobenzaldehyde (968 mg, 1.3 eq, 7.8 mmol) and stirred at room temperature for 3 hours. The reaction mixture was added with hexane, then made acidic with addition of 1 N hydrochloric acid and extracted twice with ethyl acetate. Subsequently, the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 1.23 g (yield: 92%, E:Z=99:1) of the title compound as yellow oil.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-73a8692b152b45609e2eaaf6a94e709c
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703527B2

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