3-Phenylprop-2-En-1-Ol → 3-Phenylprop-2-Enal

HRID 48550

Reaktionsgleichung

Reaktionsgleichung von HRID 48550
[CH2:1]([OH:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[N+](C1C=CC=CC=1C=O)([O-])=O.Cl>C1C=CC=CC=1.C(OCC)(=O)C>[CH:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 3083-Phenylprop-2-En-1-OlHCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 11143Aluminum isopropoxide

Produkt 1

HCID 3073-Phenylprop-2-EnalAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cinnamyl alcohol (270 mg, 2.0 mmol) was dissolved in benzene (1 mL), added with aluminum isopropoxide (40 mg, 0.1 eq, 0.20 mmol) and 2-nitrobenzaldehyde (390 mg, 1.3 eq, 2.6 mmol) and stirred at room temperature for 1 hour. The reaction mixture was added with ethyl acetate and made acidic with addition of 2 N hydrochloric acid, and then the organic layer was separated. 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=30:1) to obtain 260 mg (yield: 97%) of the title compound as yellow oil.

Aufarbeitung

  1. customthe organic layer was separated
  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=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-e0be993750554c2e8d74cf2b7b4f6647
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703527B2

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