IOWA ACADEMY OF SCIENCES. 115 



Hirsch' used the chloride instead of the sulphate, and 

 claimed to have obtained a ^neld equal in weight to 50 per 

 cent of the aniline used. He suggests that the "cause of 

 the small yield obtained by Hoffmeister was due to the 

 formation of phenol sulphonic acid. 



Merz and Weith' obtained a yield of six per cent of 

 theory by heating phenol with zinc chloride, and also a 

 small yield by heating phenol with aluminium chloride. 



Gladstone and Tribe'" obtained a good yield by distill- 

 ing alluminium phenolate. 



B. Jeitles" obtained phenyl ether by distilling calcium 

 phenyl salicylate 



Klepl" prepared phenyl ether by distilling para-phenoxy 

 benzoic acid wdth caustic baryta. 



Richter'' obtained phenyl ether by distilling sodium 

 salicylate with triphenyl phosphate. 



During the past three years, in company with some of 

 my advanced students, I have been studying the prepara- 

 tion of derivatives of phenyl ether by means of a method 

 which is of general application in both the fatty and 

 aromatic series — ^that of heating a halogen-nitro-benzene 

 with a potassium phenol. The results were published in 

 part in the Proceedings op the Academy, but mostly in 

 other journals. 



As I was about to begin the study of derivatives of 

 phenyl ether by direct methods it was important to 

 obtain the substance in considerable quantities. Having 

 attempted to follow out several original ideas of my own 

 without avail, I began to study the methods of those who 

 had already prepared the substance and selected the 

 method of Hoffmeister, as modified by Hirsch, and that of 

 Gladstone and Tribe as the most promising. 



» Berlchte XXIII. 3r0. 



« Berichte XIV, 187. 



'" Jr. Lond. Chem. Sac. XLI, .5. 



" Monats Hefte 17, 65. 



"'Jr. Pract. Chem. (2), 28, 193. 



»=■ Jr. Pract. Chem. (2), 28, 201. 



