2 Rachel Lloyd, 



In order to ascertain whether the above reactions are com- 

 mon to the benzol-series, or not, I have undertaken the con- 

 version of some of the higher homologues of benzol-phenol 

 into primary and secondary amines, with the following 

 results. 



ISOBUTYLPHENOL. 



Isobutylphenol, prepared by the method given by Lieb- 

 mann,i boiling at 230° was heated in closed tubes with zinc- 

 ammonium-bromide and ammonium-bromide in the propor- 

 tions by weight of 1:3:1 for forty hours at a temperature 

 of 320°-330°. 



The tube-contents showed indistinct layers ; the upper, an 

 amorphous mass of a dark-green color ; the under layer, a 

 semi-solid mass of a light-green color, contained an abun- 

 dance of darker particles. Accompanying these was a quan- 

 tity of a dark-green oily liquid. During the reaction water 

 was formed in abundance in the tubes. 



The opening of the tubes showed considerable pressure. 

 The escaping gas possessed an aromatic odor and burned 

 with a feeble flame. 



The tubes were further heated during six hours at the 

 same temperature ; the contents showed no special change 

 from the appearances above described, but the oily portions 

 were darker in color and the layers not so distinctly marked. 

 The treatment of the tube-contents was as follows, and this 

 method, essentially the same as that used by Merz and 

 Miiller^ for the separation and quantitative estimation of 

 mono-phenyl and diphenylamine and unchanged phenol from 

 benzol-phenol, was followed in subsequent experiments with 

 other phenols. The reactions-mass was warmed with dilute 

 hydrochloric acid until complete solution took place, with the 

 exception of floating charred particles. Floating on the 

 surface of the green-colored solution was a dark-brown oil. 

 To insure complete separation of the substances, the entire 



1 Berichte der Deutschen chem. Gesellschaft XIV., 1842. 



2 Ibid. XIX., 2902. 



98 



