반응 #81616

반응 방정식

2,2-dimethylphenethyl acetate

aluminum chloride

→

title compound

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

용매

methylene chloride

반응 조건

후처리

1. 1
   온도Place under a nitrogen atmosphere, cool to 0°-5° C.
2. 2
   기타at approximately 0° C
3. 3
   기타quench
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
   기타Separate the organic phase
7. 7
   추출extract the aqueous phase with methylene chloride (300 mL)
8. 8
   세척Combine 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
   건조Dry (MgSO4)
10. 10
    workup.STIRRINGstir for 30 minutes
11. 11
    여과before filtering
12. 12
    기타Evaporate the solvent in vacuo
13. 13
    기타purify by chromatography (ethyl acetate/hexane)

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 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.

출처