OP ARTS AND SCIENCES. 105 



of all the benzyl compounds thus far examined, and it seems to be far 

 more volatile than the corresponding para compound. It melts at 

 52-.53°, and at higher temjieraturcs sublimes slowly in oily drops 

 which soon solidify iu radiating needles. By oxidation with dilute 

 nitric acid it is converted into an acid which melts at 150-155°. 

 Since the orthoiodbenzoic acid obtained by Kekule* from orthoiodtoluol 

 melted at 155-156°, our product without doubt has the same compo- 

 sition. 



As a further proof of the constitution of orthoiodbenzylbromide 

 we made the uitril, and from it orthoiodalphatoluic acid. To form the 

 nitril the bromide was boiled with an alcoholic solution of potassic 

 cyanide. The oily liquid precipitated by the addition of water was 

 heated to 125° for four hours with fuming hydrochloric acid. When 

 cold the oil solidified, and more of the acid separated from the solution 

 in long needles. After removing the excess of hydrochloric acid, the 

 crude product was purified by crystallization from hot water. 



Orthoiodalphatoluic acid crystallizes in fine felted needles which are 

 sparingly soluble in cold, readily soluble in hot water and in alcohol, 

 ether, carbonic disulphide, and ligroin. With the limited amount of 

 material at our disposal we were unable to raise the melting point 

 above 95-90°. It would seem, however, from the analogy of the 

 orthobromalphatoluic acid that the melting point of our acid should 

 be somewhat higher. When we return to this subject and have access 

 to a larger supply of the acid, its melting point will be more carefully 

 tested. The silver salt of this acid was made by adding argentic 

 nitrate to an aqueous solution of the ammonium salt. It separated 

 from the solution as a curdy precipitate which was but slightly soluble 

 in water, readily soluble iu dilute nitric acid. For analysis it was dried 

 over sulphuric acid. 



0.2615 grm. of the salt gave by precipitation with HCl 0.1008 grm. 

 AgCl. 



Calculated for C^HJCOOAg. Found. 



Ag 29.27 29.00 



We also submitted the bromide to the action of alchoholic ammonia ; 

 but as the result of one experiment with a small quantity of substance 

 we succeeded in isolating only the primary amine. The product of 

 this reaction was treated with water, and the aqueous solution evaporated 

 on the water bath. Upon the addition of sodic hydrate the free base 



* Berichte der deutscli. chem. Gesellsch. 1874, 1007. 



