2-Ethylhexanamide

Ethylenimine, 30, 38 toxic properties of, 30, 40 Ethyl o-ethoxybenzoate, 32, 75 Ethyl formate, 32, 32 Ethyl glycidyl ether, 31, 3 2-Ethylhexanaldoxime, 32, 67 2-Ethylhexanamide, 32, 65 2-Ethylhexanoic acid, 32, 66 2-Ethylhexanonitrile, 32, 65 Ethylidene bromide, 32, 55 Ethyl iodide, 31, 34 Ethyl isodehydroacetate, 32, 76 Ethyl lactate, 31, 59, 60 5-ETHYL-2-METHYLPYRIDINE, 30, 41 Ethyl orthocarbonate, 32, 68 Ethyl orthoformate, 32, 5 Ethyl orthosilicate, 32, 5 Ethyl phenylazoacetoacetate, 32, 85 Ethyl phenylcyanoacetate, 30,43,80 Ethyl 0-phenyl-/3-cyanopropionate, 30, 84... 

Amides undergo dehydration. Useful dehydrating events include SOCI2, P Ojo (P2O5), (AcO 0, and POCI3/A. The product is a nitrile, and in fact, dehydration of an cimide is one method to produce ciryl nitriles. Figure 12-38 shows the synthesis of 2-ethylhexanenitrile from 2-ethylhexanamide with a 94-percent yield. 

The 2-ethylhexanamide was prepared in 86-88% yield from technical 2-ethylhexanoic acid (Carbide and Carbon Chemicals Corporation) by a method similar to that described previously,2 except that the crude amide was filtered directly from the reaction mixture, washed well with water, and dried. The resulting product, which melted at 99-101°, was used without further purification. If the pure amide is desired, this product may be recrystallized (with 83-90% recovery) from 50% ethanol. For 100 g. of amide, 2 1. of 50% ethanol is used, and the hot solution is decolorized with charcoal. The product thus obtained is in the form of white needles which melt at 102-103°. 

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