280 PROCEEDINGS OP THE AMERICAN ACADEMY. 



Benzyl alcohol, therefore, does not affect trinitranisol under the condi- 

 tions used in the experiment described in the last paragraph. 



Attempts to prepare Derivatives from the Addition Compound of 

 Trinitranisol and Sodic Methylate. 



Salts. — The sodium salt C6H2(NOo)30CH3NaOCH3 was treated with 

 the salts of various metals in the hope of obtaining other salts. The 

 chlorides of calcium, barium, mercury, and zinc, in mixed methyl alco- 

 holic and aqueous solutions produced no change. Cupric chloride, on 

 the other hand, formed a brown precipitate, from which trinitranisol was 

 isolated, and tests were obtained for copper and picric acid. We decided, 

 therefore, that the cupric chloride had decomposed the colored compound, 

 and neither this nor any of the other experiments we tried seemed to 

 point to the formation of salts of the colored compounds by metathetical 

 reactions. 



Treatment with Benzoyl Chloride. — The addition compound 

 CsH2(N02)aOCH3NaOCH3, if dissolved in methyl alcohol and treated 

 with benzoyl chloride, was at once decolorized, even when sodic methyl- 

 ate was also present. Upon treating the dry compound with benzoyl 

 chloride, and allowing the mixture to stand over night, the amorphous 

 powder had become converted into masses resembling cauliflowers, with 

 an even more intense scarlet color than at first. An attempt to introduce 

 the benzoyl group by the Baumann-Schotten method led to a similar result. 

 One gram of the addition product was added to 25 grams of an 18 per 

 cent solution of sodic hydrate, and then 5 grams of benzoyl chloride were 

 gradually poured into the mixture ; the granular red powder was gradu- 

 ally converted into masses resembling cauliflowers, most of which dis- 

 solved in the alkaline liquid with a distinct intensification of the red color. 

 On acidifying with hydrochloric acid, the color was discharged and a 

 white precipitate of benzoic acid was formed. The filtrate apparently 

 contained picric acid. Unfortunately we had not time to study this reac- 

 tion more carefully, but we hope it will be investigated in this Laboratory 

 during the coming year, and also that the behavior of this compound with 

 methyl iodide may be studied then. 



Postscript. The manuscript of the foregoing paper was ready for the 

 press, when I received an article * on colored compounds of this class by 

 Hantzsch and Kissel, in which they ascribe to them formulas with the 



* Ber. d. chem. Ges., XXXII. 3137 (1899). 



