58 PROCEEDINGS OF THE AMERICAN ACADEMY 



as a dark oil, made by heating chlorbenzylchloride to 120°-130° in a 

 sealed tube with potassic cyanide and alcohol ; but no attempt was 

 made to purify or analyze it. This heating in a sealed tube to 120°— 

 130° is, as seen from the above, unnecessary. 



Parachloralphatoluylic Acid, C 6 JI i ClCIf 9 COOIT, made by heating 

 the nitrile to 100° in a sealed tube with fuming hydrochloric acid, or 

 by boiling it with dilute sulphuric acid in a flask with a return-cooler, 

 was purified by solution in ammonic hydrate, precipitation with sul- 

 phuric acid, and recrystallizing from boiling water. Its composition 

 was established by an analysis of the silver salt. 



Properties. White needles, often two centimetres long, sometimes 

 thick and pointed, with a pleasant smell ; melting-point, 103^°-104° ; 

 sublimes easily in little plates, and can be distilled, although not 

 quickly, in a current of steam ; somewhat soluble in cold, much more 

 so in hot water, freely in alcohol, ether, benzole, carbonic disulphide, 

 and glacial acetic acid. Aqueous ammonia dissolves it readily, but the 

 ammonic salt is decomposed, at least in part, by evaporation the acid 

 being set free. 



A chloralphatoluylic acid has been already described as the para 

 compound by Neuhof,* who made it, however, from chlorbenzylchloride; 

 the melting-point was 60°, and it separated from its salts as an oil 

 which soon solidified, otherwise it resembled our acid, except that it 

 seems to have been much more soluble in water. Later, Radziszew- 

 ski f made a similar acid, melting at 68° by chloriring alphatoluylic 

 acid. 



Argentic Parachloralphatoluylate, C^H^WH.^COOAg, fell as a 

 white, curdy precipitate, upon adding argentic nitrate to a neutral 

 solution of the ammonic salt of the acid. It was washed with water, 

 dried at 100°, and analyzed. 



0.3410 gr. of substance gave, precipitated from a nitric acid solution, 

 with hydrochloric acid, 0.1788 gr. of AgCl. 



Calculated for C 8 H 6 C10 2 Ag. Found. 



Silver 38.91 39.44 



Properties. A white, curdy mass, consisting of clumps of silky 

 microscopic needles, which blackens rapidly in direct sunlight, but 

 only very slowly in diffused daylight ; very slightly soluble in boil- 

 ing water, almost insoluble in cold, freely soluble in dilute nitric acid 

 and ammonic hydrate. 



* Neuhof, Ann. Chem. Pharm. 147, p. 347. 

 t Radziszewski, Ber. D. Ch. G. ii. p. 207. 



