Conversion of Bcnzol-PJienol. 3 



solution was warmed with ether under reversed condenser. 

 The oil dissolved readily in the ether. The primary base 

 was sought for in the acid solution, and the secondary base 

 and unchanged phenol in the ether extract. 



The addition of an excess of ammonia to the acid solution 

 caused the separation of a light-brown oil, which after extrac- 

 tion with ether and drying over caustic potash was fraction- 

 ally distilled and weighed. 



Phcjiisobutylaniinc : — 



Nf-H ^CioHi.,.NHo. 



The larger part of the primary base — a light-brown oil, 

 had a constant boiling point of 230°-23i°. The amidoisobuty- 

 lamine obtained by Studer ^ from aniline, hydrochloric acid 

 and isobutyl-alcohol, boiled at the same temperature. The 

 acetyl compound of phenisobutylamine crystallized from warm 

 alcohol in satiny leaflets, which melted at 170°, corresponding 

 in all respects with the amine of Studer. According to the 

 investigations of Pahl,^ it seems evident that Studer's base 

 is a /> amidoisobutylamine. 



The ether extract, separated from the acid solution by 

 means of a separation funnel, was filtered to remove charred 

 particles (which particles were dried and weighed), then 

 thoroughly shaken with sodium hydrate to free the sought- 

 for secondary amine from any unchanged phenol which might 

 be present. 



DipJienisobutylamine : — 



NfC6H4.QH„=CooHo6NH. 



The so-isolated secondary amine — a thick oily liquid of a 

 deep-brown color — was twice distilled with superheated 



1 Studer, Annalen 211, 236. 



2 Berichte der Deutschen chem. Gesellschaft XVII., 1233, 



99 



