288 



Scientific Proceedings, Royal Dublin Society, 



product of the action of nitrogen peroxide vapour on the solid ether was 

 4-nitrophenylbenzylether. Small amounts of benzoic acid and tarry matter 

 were also formed. Similar results were obtained with solutions of nitrogen 

 sesquioxide and the ether. 



In dilute solution, and at the ordinary temperature, the action of nitric 

 acid on the ether was greatly affected by the nature of the solvent. When 

 dissolved in ordinary ether phenylbenzylether appeared to be unaffected by 

 dilute solutions of nitric acid in thio solvent. Similar results were obtained in 

 glacial acetic acid solutions of the substances, but when the action in the latter 

 solvent was very prolonged only decomposition products of the ether were 

 recovered. On the other hand, the substances interacted fairly easily in carbon 

 tetrachloride solution forming successively 4-nitro- and 4-4'-dinitrophenyl- 

 benzylether. 



Concentrated nitric acid, even in the cold, acted energetically on phenyl- 

 benzylether, yielding forty to fifty per cent, of its 4-nitro derivative together 

 with tarry and oily matter. 



From 4-nitro- and from 2-nitrophenylbenzylether by the direct action of 

 fuming nitric acid we obtained 2-4-4'- and 2-4-2'-trinitrophenylbenzylether. 



A mixture of concentrated sulphuric and nitric acids converted both the 

 trinitro compounds into the same pentanitro derivative, which was probably 

 2-4-6-2'-4'-pentanitrophenylbenzylether. When the latter compound was heated 

 with a mixture of fuming sulphuric and nitric acids a white crystalline 

 substance was obtained. This melted at 138-140° C, gave a reddish solution 

 in dilute aqueous alkali, and appeared to be a decomposition product of the 

 nitrated ether. 



The results obtained by us in the nitration of phenylbenzylether are shown 

 in the following diagram : — 



Phenvlbenzvlether 

 (M'.P. 39° C.J 



4-Nitropheiiylbeiizylether 

 (M.P. 10u°C.) 



V 



4'4'-Dinitrnplieiivllienzylether 

 (M.P. 186° C.) 



'2'4'4'-Triiutrop)ieiiylbenzylethei' 

 (U.V. 208° C.) 



2-4-2-Ti'initi'ophMiTll)enzyletlier 

 (M.P. 188° C.) 



I '^ 

 I 



2'4"6'2''4'-Pentanitropheiiyl!)enzylether 

 (M.P. 146°C.) 



2-NitroplienYlbenzyletlier 

 (M.P. '29° C.) 



I I 

 \ I 



