JACKSON AND TORREY. AN ORGANIC OXIDE. 165 



solved in sodic hydrate, and was reprecipitated by hydrochloric acid. 

 From its properties there can be little doubt that it is the resorcine ether 

 (CgH40H)oO, and therefore that two molecules of resorcine have taken 

 part in its formation. 



Sulphuric acid of specific gravity 1.44 had no apparent effect on chlor- 

 anilic acid. 



Sulphuric acid of specific gravity 1.44 did not act on pyrocatechine, and 

 when an acid of 1.84 specific gravitj'^ was used the substance was charred. 

 When guaiacol was boiled with sulphuric acid of specific gravity 1.44 for 

 three to four hours, the liquid turned purplish black, and on standing a 

 small quantity of a black amorphous substance separated, which we have 

 not yet succeeded in obtaining in sufficient quantity for identification ; 

 but, as it became colorless when treated with zinc and sulphuric acid, and 

 this reduction product was turned yellow by dilute nitric acid, it seems 

 certain that it is not the desired oxide ; it probably belongs to the class of 

 quinones. We hope that the study of this body will be continued in this 

 Laboratory in the coming year. In the hope tliat the loading of the ben- 

 zol ring with bromine atoms would make the substance more stable, and 

 at the same time encourage the formation of an oxide, since our oxide 

 was prepared from a body with negative radicals on the ring, we next 

 tried the action of sulphuric acid on tetrabromveratrol. With weaker 

 acids no change was observed, but, when it was heated with an acid of 

 specific gravity 1.84, a dark colored solution was formed, and sulphur- 

 ous dioxide was given off ; after dilution with water a red substance was 

 precipitated, which we inferred was tetrabromorthoquinone from its color, 

 and the fact that the sulphuric acid had given up oxygen in forming it. 

 We have not succeeded as yet in obtaining anything resembling our 

 oxide from any of the other brompyrocatechines or their ethers which we 

 have tried. 



Tetrabromguaiacol, C^T^OC HoOH, 



This substance was made in connection with the work just described 

 as follows. Five cubic centimeters of bromine (a considerable excess 

 over the four molecules required) were added slowly to 2 grams of guai- 

 acol. The reaction was very violent, hydrobromic acid being given off 

 copiously, and before all the bromine had been added the oil solidified 

 to a white mass. After the reaction had been rendered complete by 

 heating for a short time on the steam bath, the product was crystallized 

 frona hot chloroform, until it showed the constant melting point 162°-163°. 



