JACKSON AND GAZZOLO. — NITRO COMPOUNDS. 279 



gave any sign of color with sodic methylate, although the experiments 

 were tried with great care, and under conditions which gave colors even 

 with some of the less reactive nitro compounds. 



Experiments on the Replacement of the ATkijl Radical in the Colored 



Compounds. 



Action of Mdhyl Alcohol on the Benzyl Compound. — The addition 

 product of benzyl picrate and sodic benzylate, discovered by W. F. Boos 

 and one of us* was heated with methyl alcohol for about half an hour, 

 and the methyl alcohol was then allowed to evaporate at ordinary tem- 

 peratures. The product consisted of glistening scarlet crystals, which 

 were at once decolorized by hydrochloric acid, yielding a substance melt- 

 ing at 64°, and crystallizing in yellow rhombic plates from benzol. It 

 was therefore trinitranisol, and the methyl alcohol had replaced the benzyl 

 groups in the original addition compound by two methyls. 



Action of Methyl Alcohol on Benzyl Picrate. — Benzyl picrate was 

 prepared according to the method given by Boos and one of us.f The 

 melting point of this substance is 145°, not 115° as given in the paper 

 just cited; the number 115° was due to a mistake in copying the melting 

 point from the note-book. A quantity of the benzyl picrate was recrys- 

 tallized four times from boiling methyl alcohol, and after each crystal- 

 lization the melting point remained constant at 145°, thus showing that 

 the benzyl picrate is not converted into methyl picrate by methyl alcohol 

 at its boiling point. 



Action of Benzyl Alcohol on the Addition Product of Trinitranisol and 

 Sodic Methylate. — The colored compound was dissolved in benzyl alcohol 

 with the aid of gentle heat, and the mixture was allowed to stand at 

 ordinary temperatures until crystals separated. The red substance ob- 

 tained in this way was decomposed with hydrochloric acid, when the 

 product after crystallization showed the constant melting point 145°, and 

 was therefore benzyl picrate. In this case, therefore, the benzyl alcohol 

 had converted the colored methyl compound into the corresponding benzyl 

 compound. 



Action of Benzyl Alcohol on Trinitranisol. — A solution of trinitranisol 

 in benzyl alcohol was allowed to stand in a paraffin desiccator until all 

 the benzyl alcohol had evaporated ; the residue showed the melting point 

 of trinitranisol, 64°. 



* These Proceedings, XXXIII. 177. 

 t Ibid., 180. 



