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

HRID 1376911노트

반응식

HRID 1376911 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-385b042276b84f86b04694753db6ee02
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663353

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