302 Scientific Proceedings, Royal Dublin Society. 



ethyl -/:>-naphthyletlier. It is only sparingly soluble in cold alcohol or benzene, 

 but dissolves fairly easily in the hot solvents. 



(I) In Carbon Tetrachloride Solution.— A solution of 2 g. of the mononitro 

 ether in 100 g. of carbon tetrachloride was placed in a flask, and to it was added 

 2 c.c. (4 molecular amounts) of nitric acid (Sp. g. 1-52). During the addition 

 of the acid the colour changed to yellow, and finally to orange. Much solid 

 matter separated in the course of a few minutes. After 3 days the carbon 

 tetrachloride was distilled under reduced pressure. Hot alcohol and chloroform 

 extracted from the solid residue some 1-6-dinitroethyl-^-naphthylether, meltmg 

 at 144^145° C. The white solid which had not dissolved in the chloroform was 

 recrystallised from acetic acid. It melted at 216-217° C, and proved to be 

 l-8-dinitroethyl-/3-naphthylether. The two dinitro compounds were formed 

 in nearly equal amounts. 



5. Action of Nitric Acid on l-Q-Dinitroethyl-fi-napMliylether. 

 About 0-2 g. of l-6-dinitroethyl-/3-naphthylether was added slowly to 



0-8 c.c. of fuming nitric acid in a small round flask. During the reaction little 

 or no heat was evolved, but the colour of the solution became orange, and finally 

 red. On standing overnight the contents of the flask became semi-solid. The 

 mixture was poured into water, and the solid was filtered, washed, and dried. 

 It was dissolved in boiling benzene, from which it separated as glistening white 

 plates, which melted at 189-190° C, and proved to be identical with the 

 l-6-8-trinitroethyl-/3-naphthylether already described. 



When this trinitro derivative was heated to 180° C. for 8 hours in a sealed 

 tube with 30 parts of alcoholic ammonia a good yield of trinitro -j3 naphthyl- 

 amine was obtained. The latter compound separated from hot acetone as golden 

 yellow prisms, which darkened at 287° C, and melted with decomposition at 

 300-301° C. It gave on analysis the foUowng results : — 



01788 g. substance gave 31 c.c. moist nitrogen at 12° C. and 766 m.m. 

 corresponding to N 20-54 

 CioH^OeN^ requires N 20-15. 



This ether is probably identical with the trinitroethyl-,/3-naphthylether 

 already prepared by Staedel [Liebig's Ann. cexvii (1883), p. 174]. 



6. Action of Nitric Acid on l-8-Dinitroethyl-j3-naphthylether. 



An experiment similar to the last was carried out with l-8-dinitroethyl-/3- 

 naphthylether, and again a similar reddish solution of the nitrated compound 

 was formed without the evolution of much heat. After remaining overnight 

 the contents of the flask were mixed with water and the solid was filtered, 

 washed, and dried. It separated from hot benzene as colourless leaves or 

 plates, melting at 189-190° C, and identical with the l-6-8-trinitroethyl-(8- 

 naphthylether described above. 



An attempt was made to nitrate this substance still further by heating 

 0-5 g. of it with 2 c.c. of fuming nitric acid for 8 hours. The contents of 

 the flask were then allowed to remain overnight, and finally were poured into 

 water. A clear yellow solution was obtained. On evaporating the aqueous 

 solution a small amount of a brownish solid remained. This dissolved in ijotash, 

 forming a deep-red solution. It was also very soluble in water, alcohol, or acetic 

 acid, but was nearly insoluble in petroleum ether, chloroform, or benzene. 

 It could not be obtained in a pure form, and was probably a decomposition 

 product of the nitrated ether. 



