Preparation of N-nonyl-thiocyanate
A mixture of 340 ml. of ethanol and 1.52 moles of potassium thiocyanate is heated to reflux, and 1.04 moles of n-nonyl bromide is added dropwise. Reflux is continued for 2 hours after completion of the addition of the bromide. Most of the ethanol is removed by distillation, and the residue is diluted with water and extracted with ether. The combined ethereal extracts are dried over calcium chloride, and the ether is removed by distillation. Fractional distillation of the residue at 19 mm. pressure gives 67% yield of n-nonyl thiocyanate, b.p. 156-157°/19 mm.
J. Am. Chem. Soc., 57, 198 (1935)