Butyl Chloride → 2-(2-Phenoxyphenyl)hexanenitrile

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Reaction Steps

Into a 300 ml three-necked flask equipped with a stirrer, a condenser, a thermometer and an addition funnel are charged 50 ml of dimethyl sulfoxide and 7.4 g (0.15 mole) of sodium cyanide. A solution of 30 g (0.14 mole) of o-phenoxybenzyl chloride in 10 ml of dimethyl sulfoxide is added dropwise at room temperature. The reaction mixture is stirred for 11/2 hours. Butyl chloride (18.7 g, 0.14 mole) is then added to the reaction mixture followed by dropwise addition of 34.3 g (0.43 mole) of 50% sodium hydroxide solution. Reaction temperature increased to 52° after the addition and stirring is continued for 1 hour. The reaction mixture is then diluted with 150 ml of water and extracted with hexane. The combined hexane extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 32 g of product. The product can be further purified by vacuum distillation (b.p. 137-142/0.2 mm).

Provenance & Evidence