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

HRID 48545

Reaktionsgleichung

Reaktionsgleichung von HRID 48545
[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-].[N+](C1C=C(C=CC=1)C=O)([O-])=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 74493-NitrobenzaldehydeHCID 11143Aluminum isopropoxideHCID 445070Farnesol

Produkt 1

HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienalAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol (445 mg, 2.0 mmol) was dissolved in cyclohexane (1 mL), added with aluminum isopropoxide (40 mg, 0.1 eq, 0.2 mmol) and 3-nitrobenzaldehyde (393 mg, 1.3 eq, 2.6 mmol) and stirred at room temperature for 2 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 427 mg (yield: 96%, 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-e95a46d4355c47f6afb7014336a8dda3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703527B2

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