Hydrochloric Acid → Perillaldehyde

HRID 48551

Reaktionsgleichung

Reaktionsgleichung von HRID 48551
[CH3:1][C:2]([C@@H:4]1[CH2:9][CH:8]=[C:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)=[CH2:3].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>[CH3:3][C:2]([CH:4]1[CH2:5][CH:6]=[C:7]([CH:10]=[O:11])[CH2:8][CH2:9]1)=[CH2:1]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 111012-NitrobenzaldehydeHCID 11143Aluminum isopropoxideHCID 369312Perilla alcohol

Produkt 1

HCID 16441PerillaldehydeAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-(−)-Perillyl alcohol (300 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 2 hours. 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 250 mg (yield: 84%) 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-3b9cccf736d040ea8ba2282804b3798f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703527B2

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