反应详情

A 1 L round bottom flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with 28.4 g anhydrous potassium carbonate (pulverized with mortar and pestle), cesium carbonate (catalytic amount), 4-(hydroxy)phenyl acetonitrile (18.26 g.), cyclohexylmethylbromide (36.4 g.) and dimethylformamide (600 mL). The mixture was heated to reflux and maintained for one week at this temperature under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature and saturated aqueous NaCl and ethyl acetate were added. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic fractions were washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated in a rotary evaporator. The crude product was partitioned between equal volumes of hexane and 25% aqueous NaOH. This mixture was stirred under nitrogen atmosphere at room temperature for three days. The aqueous layer was drawn off, and the organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give 23 g of 4-(cyclohexylmethoxy)phenylacetonitrile as a yellow solid (73% yield). This material was homogeneous by TLC (CH2Cl2) and was carried on directly to the next step without further purification.

1. customA 1 L round bottom flask equipped with a magnetic stirrer
2. temperaturereflux condenser and nitrogen inlet
3. temperatureThe mixture was heated
4. temperatureto reflux
5. temperaturemaintained for one week at this temperature under a nitrogen atmosphere
6. customThe layers were separated
7. extractionthe aqueous phase was extracted with ethyl acetate
8. washThe combined organic fractions were washed with saturated aqueous NaCl
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in a rotary evaporator
12. customThe crude product was partitioned between equal volumes of hexane and 25% aqueous NaOH
13. washthe organic layer was washed with saturated aqueous NaCl
14. dry with materialdried over MgSO4
15. filtrationfiltered
16. concentrationconcentrated