IOWA ACADEMY OF SCIENCES. 
97 
2-nitro-4'-methyl phenyl ether 
N0 2 
< > — O— < > 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: 
ISr0 2 .C 6 H i Br-fK0.C 6 H 4 .CH 3 =Id0 ;i .C 6 H 4 0C 6 H 4 .CH3+KBr. 
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, 1878), 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 
were 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. 
