N Amyl cyanide

Into a 500 ml. three-necked flask, provided with a mechanical stirrer, a gas inlet tube and a reflux condenser, place 57 g. of anhydrous stannous chloride (Section 11,50,11) and 200 ml. of anhydrous ether. Pass in dry hydrogen chloride gas (Section 11,48,1) until the mixture is saturated and separates into two layers the lower viscous layer consists of stannous chloride dissolved in ethereal hydrogen chloride. Set the stirrer in motion and add 19 5 g. of n-amyl cyanide (Sections III,112 and III,113) through the separatory funnel. Separation of the crystalline aldimine hydrochloride commences after a few minutes continue the stirring for 15 minutes. Filter oflF the crystalline solid, suspend it in about 50 ml. of water and heat under reflux until it is completely hydrolysed. Allow to cool and extract with ether dry the ethereal extract with anhydrous magnesium or calcium sulphate and remove the ether slowly (Fig. II, 13, 4, but with the distilling flask replaced by a Claisen flask with fractionating side arm). Finally, distil the residue and collect the n-hexaldehyde at 127-129°. The yield is 19 g. 

For practice, the student should carry out both alkaUne (compare Section 111,83) and acid hydrolysis of acetonitrile, n-valeronitrile (n-butyl cyanide) and n-capronitrile (n-amyl cyanide). 

Ammonolysis, 401 Ampoules, glass. 205 n-Amylamine, 413, 417 n-Amyl acetate, 383 -Amyl alcohol, 247, 249 n-Amylbenzene, 511, 517 n-Amyl borate, 305 n-Amyl bromide, 279 tao-Amyl bromide, 279 n-Amyl chloride, 273 tao-Amyl chloride, 273 tert.-Amyl chloride, 275 n-Amyl cyanide, 407, 408 Amylene, 239 n-Amyl fluoride, 272, 289 n-Amyl iodide, 288 n-Amyl nitrite, 302, 306... 

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