98 
DR. A. W. HOFMANN’S RESEARCHES REGARDING THE 
H I H 
H In into C12H5 
have been unsuccessful up to the present moment. I had hoped that this conversion 
mig-ht be effected by the action of phenyl-alcohol on aniline according to the follow- 
ing equation : — 
H ' 
r ^ 1 
H 
>N-hHO, 0,=\c,,U, > 
^12 
N+2HO. 
Phenyl-alcohol, however, has neither at the common nor at a high temperature — 
the mixture was exposed for several days in a sealed tube to 250° in an oil-bath — any 
action upon aniline. The residuary aniline was identified by analysis. When con- 
verted into a platinum-salt — 
0’3120 grrn. of the salt left on ignition 0T024 grm. of platinum. 
Experimental percentage of platinum. Theoretical percentage in the aniline-platinum-salt. 
32-82 32-98 
This experiment, when repeated for a longer period, might possibly give a more 
satisfactory result. It is known that ammonia, by a similar treatment with phenyl- 
alcohol, is likewise only very slowly converted into aniline. 
The action of chloride and bromide of phenyl Cjg H5 Cl, and ® upon aniline 
promised a better result ; but the difficulties which I encountered in preparing these 
compounds, which are as yet but very imperfectly investigated, deterred me from 
farther pursuing this direction of the inquiry. 
Much more successful were my endeavours to substitute methyl, ethyl and amyl 
for the remainder of the basic hydrogen in aniline. The compounds of these radicals 
with chlorine, bromine and iodine appeared to be the most appropriate substances for 
this purpose, I have worked with these three classes of compounds, but finding that 
the use of the chlorides and iodides is attended with inconveniences, the former com- 
pounds being exceedingly difficult to handle on account of their volatility, while the 
latter often complicate the reactions by the rapid decomposition of the hydriodic 
acid formed in the process, I have almost exclusively employed the bromides, whose 
action is so precise and definite as to preclude the necessity of seeking any farther 
agent ; only when working in the methyl-series I have sometimes preferred to employ 
the iodide, which is far less volatile than the bromide. Still the deportment of the 
iodides presents some peculiarities, which require farther elucidation. 
Action of Bromide of Ethyl upon Aniline. 
On adding dry bromide of ethyl to aniline, no change takes place in the cold, but 
on gently heating the mixture in an apparatus which will allow the volatilized bro- 
mide to return to the aniline, a lively reaction ensues. The liquid remains for some 
time in a state of ebullition, and solidifies on cooling into a mass of crystals. If a 
