Aluminum(III) Chloride → 4-(4-Chloro-1-oxobutyl)-2,2-dimethylphenethyl acetate

HRID 267069

Reaktionsgleichung

Reaktionsgleichung von HRID 267069
[Cl-:1].[Al+3].[Cl-].[Cl-].[C:5]([O:8][CH2:9][CH2:10][CH:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1([CH3:18])[CH3:17])(=[O:7])[CH3:6]>C(Cl)Cl>[C:5]([O:8][CH2:9][CH2:10][CH:11]1[CH:16]=[CH:15][C:14]([C:9](=[O:8])[CH2:10][CH2:11][CH2:12][Cl:1])=[CH:13][C:12]1([CH3:18])[CH3:17])(=[O:7])[CH3:6]

Komponenten

4

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 229063012,2-Dimethylphenethyl acetate

Produkt 1

HCID 229063004-(4-Chloro-1-oxobutyl)-2,2-dimethylphenethyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Charge a flask with aluminum chloride (223 g, 1.68 mol) and methylene chloride (200 mL). Place under a nitrogen atmosphere, cool to 0°-5° C. and add, by dropwise addition, ω-chlorobutyryl chloride (188.6 g, 1.34 mol). After acid chloride addition is complete, add, by dropwise addition, 2,2-dimethylphenethyl acetate (128.0 g, 0.67 mol), keeping the temperature at approximately 0° C. Continue stirring at 0° C. for 2 hours, quench by slowly pouring over approximately 2 L of crushed ice. Add methylene chloride (500 mL) and stir for 5 minutes. Separate the organic phase and extract the aqueous phase with methylene chloride (300 mL). Combine the organic phases and wash with saturated aqueous sodium hydrogen carbonate (3×200 mL), with deionized water (200 mL) and brine (200 mL). Dry (MgSO4) and stir for 30 minutes before filtering. Evaporate the solvent in vacuo and purify by chromatography (ethyl acetate/hexane) to give the title compound as an orange/brown oil.

Aufarbeitung

  1. temperaturePlace under a nitrogen atmosphere, cool to 0°-5° C.
  2. customat approximately 0° C
  3. customquench
  4. additionby slowly pouring over approximately 2 L of crushed ice
  5. stirringAdd methylene chloride (500 mL) and stir for 5 minutes
  6. customSeparate the organic phase
  7. extractionextract the aqueous phase with methylene chloride (300 mL)
  8. washCombine the organic phases and wash with saturated aqueous sodium hydrogen carbonate (3×200 mL), with deionized water (200 mL) and brine (200 mL)
  9. dry with materialDry (MgSO4)
  10. stirringstir for 30 minutes
  11. filtrationbefore filtering
  12. customEvaporate the solvent in vacuo
  13. custompurify by chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-280c4760bfa64107a2baf42f4066b814
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652370

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