104 PROCEEDINGS OF THE AMERICAN ACADEMY 



The crude product was washed with sodic hydrate and acetic acid, 

 and lastly with water. It was then dried over calcic chloride, and 

 finally purified by fractional distillation. In this way from 20 grms. 

 orthotoluidin we obtained before fractioning 28 grms. orthoiodtoluol, 

 which gave 20 grms. boiling at 211° (mercury column wholly in 

 vapor).* 



To convert orthoiodtoluol into orthoiodbenzylbromide, 10 grms. 

 were heated to 190-200° under a return condenser, and 10 grms. 

 bromine allowed to run into the flask from a drop funnel as rapidly as 

 it was absorbed. On cooling, the product of the reaction formed a 

 thick oily liquid which did not solidify at 0°. It was therefore washed 

 with a dilute solution of sodic hydrate, to remove the iodine which was 

 invariably set free during the bromiring, and distilled in the vapor of 

 concentrated hydrobromic acid according to the method followed by 

 Professor Jackson in the purification of orthobrombenzylbromide.f 

 The distillate solidified when cooled with snow, and after removing 

 the oil by pressure in filter paper, it was purified by crystallization 

 from ligroin. 



The composition of this substance was established by the following 

 analyses : — 



I. 0.1994 grm. of the substance gave 0.3945 grm. Ag Br -|- Ag I. 

 II. 0.2793 grm. of the substance gave 0.3945 grm. Ag Br -|- Ag I. 

 III. 0.3246 grm. of the substance gave 0.3350 grm. CO2 and 0.0674 

 grm. Hp. 



Calculated for C^H^Brl. Found. 



I. II. III. 



28.16 

 2.30 



69.53 69.11 



Orthoiodbenzylbromide is readily soluble in ether, hot alcohol, benzol, 

 carbonic disulphide, and chloroform. It is nearly, if not quite, insolu- 

 ble in water, and very sparingly soluble in cold ligroin. From a cold 

 saturated solution in ligroin it crystallizes in flattened prisms often 2 or 

 3 centimeters in length. AVhen crystallization takes place from a hot 

 solution it appears in the form of short thick prisms. The vapor of 

 this substance affects the mucous membrane in the same way as that 



* Kekulc, Beriehte der deutsch. cliem. Gesellsch. 1874, 1007. 

 t These Proceedings, Vol. XII. p. 217. 



