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

HRID 263731ノート

反応式

HRID 263731 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-34f83424a85f48349108c19496c8de6d
出典データセット
uspto-grants-1997_07
特許番号
US05644061

反応ノート

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