Sodium Chloride → 4-(Cyclohexylmethoxy)phenylacetonitrile

Participants

Reaction Steps

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.

Provenance & Evidence