Preparation of 2-cyanooctane
30 g of dry sodium cyanide (dried at 110º C overnight a) are mixed with 150 ml of dry dimethyl sulfoxide. The mixture is added to the flask fitted with a stirrer, reflux condenser, dropping funnel, and thermometer. The thick reaction slurry is heated to 130º C and the heating then is stopped. 0.5 mole of 2-chlorooctane is slowly added to the stirred mixture during 30 min. The temperature of the refluxing reaction mixture slowly increased as nitrile was formed. Refluxing continued as the temperature slowly rose to 135 ºC after 1 hr. reaction time. After the reaction is complete the mixture is poured into water and the product extracted several times with chloroform or ethyl ether. The extract is washed several times with saturated sodium chloride solution, dried over calcium chloride, and the 2-cyanooctane is distilled at 88 ºC/12mmHg yielding 70% of the final product.
J. Org. Chem., 1960, 25 (2), pp 257–258