反応 #81616

反応方程式

2,2-dimethylphenethyl acetate

aluminum chloride

→

title compound

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

溶媒

methylene chloride

反応条件

後処理

1. 1
   温度Place under a nitrogen atmosphere, cool to 0°-5° C.
2. 2
   その他at approximately 0° C
3. 3
   その他quench
4. 4
   workup.ADDITIONby slowly pouring over approximately 2L of crushed ice
5. 5
   workup.STIRRINGAdd methylene chloride (500 mL) and stir for 5 minutes
6. 6
   その他Separate the organic phase
7. 7
   抽出extract the aqueous phase with methylene chloride (300 mL)
8. 8
   洗浄Combine the organic phases and wash with saturated aqueous sodium hydrogen carbonate (3×200 mL), with deionized water (200 mL) and brine (200 mL)
9. 9
   乾燥Dry (MgSO4)
10. 10
    workup.STIRRINGstir for 30 minutes
11. 11
    ろ過before filtering
12. 12
    その他Evaporate the solvent in vacuo
13. 13
    その他purify by chromatography (ethyl acetate/hexane)

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 2L 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.

出典