310 - Scientific Proceedings, Royal Dublin Society. 



7. Action of Nitric Acid on 2-4-8-10-Tetranitrodiphenylethyleneether. 



Tetranitrodiphenylethyleneether was heated for an hour and a half on 

 the water-bath with 5 pax'ts of mixed acids, and the mixture was then poured 

 into water. 



The product consisted mainly of unchanged tetranitrodiphenylethylene- 

 ether together with a small amount of 2'4-dinitrophenol, melting at 114° C. 



8. Synthetical Preparations of the Nitro Derivatives. 



(a) 2-Nitrodiphe7iylethyleneether. — Phenylbromethylether (10 g.), which 

 was prepared from ethylene dibromide and potassium phenolate by the method 

 of W. H. Perkin [Joum. Chem. Soc, Ixix (1888), p. 165-6], was added to 

 a solution of potash (3 g.) and 2-nitrophenol (8 g.) in alcohol (50 g.), and 

 the mixture was heated to gentle boiling under a reflux condenser for 16 

 to 18 hours. The residue left after distillation of the alcohol was washed 

 with water and recrystallised several times from alcohol. It melted at 

 97° C. and gave on analysis the following results : — 



0181 g. substance gave 86 c.c. moist nitrogen at 16° C. and 753 m.m. 



corresponding to N 56 

 C^HisO^N requires N5-4. 



2-Nitrodiphenylethyleneether crystallises from alcohol in the form of 

 rectangular plates which are sparinglj^ soluble in cold alcohol, soluble 

 in ether, and readily soluble in hot alcohol or chloroform. It is insoluble in 

 aqueous potash. 



(&) 4-Nitrodiphenylethyleneether. — A solution of 2 g. potash and 6 g, 

 4-nitrophenol and 10-5 g. of phenylbromethylether in 50 g. of alcohol was 

 heated under a reflux condenser for 24 hours. The alcohol was removed 

 by distillation, and the product v/as freed from potassium bromide and excess of 

 4-nitrophenol by washing with dilute alkali. After several recrystallisations 

 from alcohol it melted at 86° C, and gave on analysis the following results : — 



0-209 g. substance gave 101 c.e. moist nitrogen at 16° C. and 757 m.m. 



corresponding to N 569 



C14H13O4N requires N 5-4. _ _ _ 



4-Nitrodiphenylethyleneether crystallises from ether and alcohol in the 

 form of prisms which are insoluble in potash, soluble in alcohol, chloroform, 

 and acetone, sparingly soluble in ether. 



(c) 2-10-Dinitrod.iphenylethyleneether. — 2-Nitrophenylbromethylether, which 

 was prepared from 2-nitrophenoI and ethylene dibromide by the method already 

 described by Weddige [Journ. f. pr. Ch. (2), xxiv (1881), p. 246], was heated 

 for 26 hours under a reflux condenser with an alcoholic solution of the potassium 

 derivative of 4-nitrophenol. The alcohol was then distilled, and the residue 

 was washed with dflute potash until it was free from potassium bromide and 

 4-nitrophenol. After reerystallisation from alcohol the substance melted at 

 117-5° C. It gave on analysis the following results : — 



0184 g. substance gave 15-2 c.c. moist nitrogen at 15° C. and 760 m.m. 



corresponding to N 96 

 C^HijOeN, requires N 9-2. 



