300 Scientific Proceedings, Royal Dublin Society. 



from which it separated as creamy-white plates, melting at 102-103° C, and 

 consisting of l-nitroethyl-j3-naphthylether. The red oily matter did not 

 crystallise. 



By the action of nitrogen peroxide on ethyl-/3-naphthylether in carbon 

 tetrachloride solution l-8-dinitroethyl-/3-naphthylether (60 per cent.) was the 

 main product, whilst l-nitroethyl/3-naphthylether (10 per cent.) and oils (30 

 per cent.) were also fonned. 



2. Action of Nitrous Fumes on Ethyl -j3-napMhylether. 



Nitrous fumes, generated by the action of nitric acid on arsenious oxide, 

 passed for half an hour into a solution of 2 g. of etliyl-/3-naphthylether 

 in 50 g. of 95 per cent, acetic acid. A crystalline solid gradually separated, 

 and this was, after ten days, filtered. The crystals proved to be 1-nitroethyl- 

 /3 - naphthylether. When the red filtrate was poured into water, an orange 

 precipitate was obtained. This also proved to be l-nitroetliyl-/3-naphthyl ether. 



In a similar experiment in which glacial acetic acid was the solvent, we 

 obtained finally a dark oilj^ residue which did not crystallise. 



3. Action of Nitric Acid on Ethyl -(i-naphthylether. 



(a) In the Absence of Solvents. — 3 g. of ethyl-|3-naphthylether was added 

 slowly to 12 c.c. of fuming nitric acid (Sp. g. 1-52) in a small round flask. 

 The addition resulted in the production of a red solution with the evolution 

 of much heat. The contents, which were not allowed to rise above 15° C, 

 were let stand overnight and then poured into water. An orange-red pre- 

 cipitate was formed, which was filtered, washed, and dried. The dry solid, 

 on fractional crystallisation from warm alcohol, gave two portions, one more 

 soluble, melting at 125-130° C, and the other less soluble, melting at 180- 

 197° C. After reci-ystallising both mixtures from glacial acetic acid, colourless 

 needles, melting at 143-144° C, together mth platy prisms, melting at 216° C, 

 were obtained, which proved identical with 1-6- and l-8-dinitroethyl-/3- 

 naphthylether respectively. By the action of nitric acid, then, on ethyl -/j- 

 naphthylether, the 1-6- and IS-dinitro derivatives were formed in nearly equal 

 parts, together with a little (0-1-0-2 g.) red oily matter. In a similar experiment 

 in which the temperature was allowed to rise to 50-55° C, the 1-6-8-trinitro 

 derivative was the only crystalline product with 0-4-0-5 g. of oily or brown 

 tarry matter. 



(&) In Acetic Acid Solution. — 045 c.c. (1 molecular amount) of nitric acid 

 (Sp. g. 1-52) was added to a solution of 2 g. of ethyl-/3-naphthylether in 

 50 g. of glacial acetic acid. The solution was at first clear yellow in colour, 

 but on short standing in a stoppered flask it deepened to red. After 2 days 

 0-2 of yellow crystals separated. These melted at 103-4° C. after recrystallisa- 

 tion from alcohol, and proved to be l-nitroethyl-/3-naphthyl ether. 



After separating the crystals by filtration, the parent liquid was returned 

 to the stoppered flask. No further change occurred during the following week. 

 The clear red solution was then poured into water, and the resulting precipitate 

 was isolated, washed with water, and dried. The dried mass, after recrystallisa- 

 tion from alcohol, melted at 103-4° C, and was identical with l-nitroethyl-/3- 

 naphthylether. 



Similar experiments were undertaken with 2, and also with 4, molecular 

 amounts of nitric acid (Sp. g. 1-52), but in each case l-nitroethyl-/3-naphthylether 

 formed the only nitration product. 



(c) In Carbon Tetrachloride Solution. — 045 g. (1 molecular amount) of nitric 



