118 IOWA ACADEMY OF SCIENCES. 



did not study the compound exhaustively, I think it likely 

 has the formula, Ce H5 No NH.CeHs. I do not know that 

 this compound has been obtained up to this time, but the 

 corresponding para-toluidine compound is known, On 

 fractionating the substance several times a portion weigh- 

 ing several grams was obtained, which boiled between 

 180° and 182°. On standing decomposition took place. 

 When first prepared it had no odor and was colorless, but 

 on standing for three months it became dark in color and 

 had a strong odor of phenol. All but a few globules dis- 

 solved in caustic potassa. These globules had the charac- 

 teristic odor of phenyl ether. There was not enough of 

 this oil to collect and determine its melting point. The 

 change took place in two portions, one iu an open flask and 

 the other in a fall and tightly corked bottle. The action 

 was not, therefore, due to the oxidizing action of the air. 



Second experiment: 

 Quantities taken, 



Aniline 100 grams. 



Concentrated hydrochloric acid 200 grams. 



Water 700 grams . 



Phenol containing 10 per cent of water 500 grams. 



The diazo solution was added slowly while the phenol 

 solution was heated to 53° — 63°. This was the only differ- 

 ence between this trial and the preceding one. 



Results were obtained as follows: 



1. None of the substance boiling at 180° -182°. 



2. About eight grams of purified phenyl ether. 



3. Much less of the crystalline solid. 



4. A great deal of tar. 



Th ird expert meyit : 

 Quantities taken, 



Aniline 100 grams. 



Water 1 , 000 grams . 



Phenol containing 10 par cent of water 450 grams. 



Concentrated hydrochloric acid, sufficient to diazotize the aniline. 



In this experiment the phenyl ether was distilled from 

 the higher boiling substances with steam. The yield was 



