Reacción #81616

Ecuación de reacción

2,2-dimethylphenethyl acetate

aluminum chloride

→

title compound

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

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaPlace under a nitrogen atmosphere, cool to 0°-5° C.
2. 2
   Otroat approximately 0° C
3. 3
   Otroquench
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
   OtroSeparate the organic phase
7. 7
   Extracciónextract the aqueous phase with methylene chloride (300 mL)
8. 8
   LavadoCombine 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
   SecadoDry (MgSO4)
10. 10
    workup.STIRRINGstir for 30 minutes
11. 11
    Filtraciónbefore filtering
12. 12
    OtroEvaporate the solvent in vacuo
13. 13
    Otropurify by chromatography (ethyl acetate/hexane)

Procedimiento

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.

Fuente