IOWA ACADEMY OF SCIENCES. 



2-nitro-4'-methyl phenyl ether 



NO., 



<C__>-0-< >CH. 



This compound was prepared by the action of o-brom 

 nitro benzene on potassium p-cresolate and the reaction 

 takes place according to the following equation: 



N0...aH,Br+K0.CaH,.CH3=N0,.aH.0CVH,.CH3+IvBr. 



The potassium p-cresolate was made by treating one 

 part of p-cresol with a molecular equivalent of potassium 

 hydroxide dissolved in one part of water, evaporating to 

 dryness on the water bath, with continual stirring and 

 then drying in the air bath at 100 °C. for half an hour. 

 This method yielded a very good product, which was of a 

 slight yellow color. An endeavor to prepare the cresolate 

 by dissolving metallic potassium in the cresol, as did 

 Haeussermann and Teichmann (Ber. 29, 1446), and F. Ull- 

 mann (Ber. 29, 1S7S), with phenol in making derivatives 

 of diphenyl ether, yielded a dark tarry product which very 

 materially effected the yield and purity of the diphenyl 

 ether which was made from it. The above mentioned 

 ether was made in the following manner: One part by 

 weight of potassium p-cresolate was heated in a small 

 Florence flask on a fusible metal bath with three parts of 

 o-brom nitro benzene to 125-130° C. when a vigorous 

 action began, accompanied by a rise of temperature of sev- 

 eral degrees. As soon as the action had ceased, which 

 required about five minutes, the melt was cooled and 

 extracted with ether. The above mentioned ether extract 

 was washed with potassium hydroxide solution to remove 

 any free cresol which might be present. The excess of 

 o-brom-nitro benzene was distilled off with steam, and the 

 phenyl ether was distilled under diminished pressure to 

 free it from any remaining trace of ortho-brom nitro ben- 

 zene, and the solid, and higher boiling substances which 

 w^ere extracted with the sulphuric ether. Under a pres- 

 sure of 25 mm. o-brom nitro benzene boils at 150° C, 

 while 2-nitro-4'-methyl phenyl ether boils at about 220° C. 



