2-Phenylethyl Acetate → 4-Octanoylphenethyl acetate

HRID 617845Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 617845
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:7])[CH3:6].[C:17](Cl)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]CC>ClC(Cl)C>[C:5]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=1)(=[O:7])[CH3:6]

Komponenten

5

Edukt 3

HCID 76542-Phenylethyl AcetateHCID 66982Decanoyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 217075284-Octanoylphenethyl acetateAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Aluminum chloride (111.8 g) was added to dichloroethane (500 ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (91.8 g) and decanoyl chloride (100 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give 61.3 g of the subject compound (yield 38%) as an oily substance.

Aufarbeitung

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionextracted with diethyl ether
  4. washThe ether layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled away
  7. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20)

Quellen und Nachweise

ORD-Eintrag
ord-1b07649e4c894bc7a47b83e49796b444
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952316

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