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benzyl alcohol therefore acts with sodium much more slowly than 

 any of the other alcohols used by us. In this way we obtained a 

 benzol * solution of the sodic benzylate, which remained clear after 

 it had cooled until it was shaken, when the solid separated in a 

 gelatinous state. To the mixture of gelatinous sodic benzylate and 

 benzol thus obtained a benzol solution of 9 gr. of tribromtrinit.ro- 

 benzol was added ; that is, for each molecule of tribromtrinitroben- 

 zol we used three molecules of sodic benzylate. f The mixture was 

 allowed to stand in the cold over night, the orange-red solution thus 

 formed evaporated to dryness on a steam radiator at temperatures 

 below 70°, and the residue washed with water and afterward with 

 alcohol, after which it was purified by crystallization from a mix- 

 ture of benzol and alcohol, until it showed the constant melting 

 point 171°. The analyses of the substance dried at 100° gave the 

 following results : — 



I. 0.2038 gr. of the substance gave on combustion 0.4546 gr. 

 of carbonic dioxide and 0.0752 gr. of water. 

 II. 0.2678 gr. of the substance gave 18.8 c.c. of nitrogen at a tem- 

 perature of 25° and a pressure of 765.3 mm. 



The substance gave no test for bromine when heated with cupric 

 oxide. 



10 gr. of tribromtrinitrobenzol gave only 1.5 gr. of the tribenzyl- 

 ether of trinitrophloroglucine, the analysis of which is given above, 

 that is, less than 13 per cent of the theoretical yield. This sub- 

 stance, therefore, is not by any means the principal product of the 

 reaction. What the other products are will be discussed after the 

 description of the properties of the benzylether. 



Properties of the Trinitrophloroglucine Tribenxylether. — This 

 substance crystallizes from a mixture of alcohol and benzol in slen- 



* Since this part of our work was finished, Briilil and Biltz have puhlished 

 similar observations on other alcoholates in Ber. d. ch. Ges., XXI. 649 (1891). 



t The same principal product was obtained in a subsequent experiment with 

 only two molecules of sodic benzylate. In most cases a slight excess of benzyl 

 alcohol was used. 



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