OF ARTS AND SCIENCES. 203 



more definite form to Beilstein's rule about the action of bromine on 

 toluol and its liomologues.* At temperatures above 150°, I observed 

 the liberation of iodine, but, as already stated in the first paper on this 

 subject, paraiodbenzylbromide was formed, although according to Beil- 

 stein t bromine enters the ring even at the boiling-point of toluol, if 

 iodine has been added. This exception to Beilstein's rule has suggested 

 a series of experiments, which will be carried on in this laboratory, 

 to determine what efi:ect, if any, the nature and position of the radical 

 attached to the main ring exercise upon the bromiring of substituted 

 toluols. 



The following substances were obtained from paraiodbenzylbromide 

 by the usual metathetical reactions: — 



Paraiodbenzylalcohol, C^H^ICH.^OH, was prepared from the product 

 of the action of sodic acetate on the bromide, by heating it to 160^ 

 with aqueous ammonia in a sealed tube : the solid thus obtained was 

 purified by pressing between filter-paper, and crystallization from car- 

 bonic disulphide. It was also made % by boiling paraiodbenzylbromide 

 with water for several hours in a l^ask with a return-condenser: that 

 hydrobromic acid was set free, was proved by the acid reaction of the 

 water, and the precipitate of argentic bromide formed on adding 

 argentic nitrate to it, after the organic matter had been removed. 



The alcohol prepared according to the first method was analyzed. 



0.2508 gr. substance gave 0.3260 gr. CO^ and 0.0633 gr. H^O. 



Properties. It crystallizes from carbonic disulphide or alcohol in 

 small silky white scales ; from boiling water, in long needles, with an 

 aromatic odor like that of the corresponding bromine compound, but 

 no action on the eyes; melting-point, 71|° ; very slightly soluble ia 

 cold, somewhat more soluble in hot water; freely in alcohol, ether, 

 benzole, and carbonic disulphide. 



The paraiodbenzylacetate was not obtained pure, because, on account 

 of its instability, a great quantity of substance would have been con- 



* These numbers liave been tested and confirmed in this laboratory' by Mr. 

 A. W. Field, who will publish his results in detail, as well as similar experiments 

 upon other substituted toluols, in a later paper of this series. — [C. L. J] 



t Ann. Cliem. Pharm. 143, p. 369. 



J These Proceedings, Vol. XII. (n. s. IV.) p. 221. 



