NEF. NITROPARAPPINE SALTS. 143 



tion immediately acidified with dilute sulphuric acid and extracted 

 with ether. After drying the ethereal solutious with calcic chloride, 

 and getting rid of the ether at reduced pressure, 10.1 grams of neutral 

 products and 9 grams of acid products are obtained. 



On allowing the oily acid portion to stand in the air, crystals of 

 ethylnitrolic acid (1 gram) separated out, and the oil gave, on treat- 

 ment with alcoholic potash, 5.3 grams of potassic dinitroethane, which 

 was filtered off. The deep red colored filtrate gave, on acidifying and 

 extracting with ether, 0.4 gram more of ethylnitrolic acid. The acid 

 products formed in the above reaction are therefore dinitroethane and 

 ethylnitrolic acid. The latter substance melted at 88°, and was iden- 

 tical in every respect with a preparation made from nitroethane.* 

 This substance gives on treating in alkaline solution with benzoyl- 

 chloride f a characteristic insoluble benzoate. 



Ethylnitrolic Acid Benzoate, CHg — C = NOCOCeHs- 



I 

 NO, 



12.1 grams ethylnitrolic acid, dissolved in 46 c.cm. sodic hydrate 

 (1 : 10), and shaken with 16.4 grams benzoylchloride gave 21.6 grams 

 crude benzoate (calculated 24.2 grams). Crystallized twice from 

 benzene, and twice from alcohol, it is obtained in colorless flat needles, 

 melting at 135° ; it is easily soluble in hot benzene and alcohol, and 

 very slightly in ether. It is insoluble in water, and is decomposed 

 slowly on standing with sodic hydrate into benzoic acid and ethyl- 

 nitrolic acid. 



0.1585 gram, dried at 70°. gave 0.3001 gram COg and 0.0604 gram HgO. 

 0.1995 gram, dried at 70°, gave 24 c.cm. Ng at 16° and 750 mm. 



The above mentioned portion (10.1 grams), insoluble in alkalies, is 

 also a mixture of two substances. It was first distilled with steam, 

 whereby all but a trace of yellow sticky material is easily carried 

 over ; the first portions of the distillate contain oil drops, which do not 

 solidify, and the latter portions contain a substance which solidifies in 



* Ann. Chem. (Liebi^), CLXXV 94, CLXXXI. 2. 



t Baumann and Udranzsky, Ber. d. chem. Ges., XXI. 2744. 



