56 PROCEEDINGS OF THE AMERICAN ACADEMY 



100.00 100.62 



Properties. White lustrous prisms or needles, often more than 3 cm. 

 long, with an agreeable aromatic odor and most violent action on the 

 mucous membrane and tenderer parts of the skin ; nielting-point, 29° ; 

 so volatile that a crystal exposed to the air disappears in a few hours ; 

 sublimes even at ordinary temperatures in needles ; it is very little, if 

 at all, soluble in water, but readily in warm, less so in cold, alcohol, 

 very easily in ether, benzole, carbonic disulphide, and glacial acetic 

 acid. That it is a chlorbenzyl compound was proved by boiling it 

 for some time with water, in a flask with a return-cooler, when the 

 parachlorbenzylalcohol and hydrochloric acid were formed. Boiled 

 with a solution of potassic permanganate, it was easily oxidized, giving 

 an acid which melts between 233° and 235° (O. Emmerling gives 234° 

 as the melting-point of parachlorbenzoic acid) ; this acid boiled with 

 water, in which the orthochlorbenzoic acid is much more soluble than 

 the para, gave a solution which deposited crystals melting also at 

 233°-235°: as potassic permanganate oxidizes instead of destroying 

 the ortho compounds, this proves that our parachlorbenzylchloride is 

 perfectly free from isomeric impurities. 



Having thus proved that the parachlorbenzylchloride used as a 

 starting-point for the preparation of derivatives by Beilstein, Kuhl- 

 berg, Neuhof, and others, really did contain the ortho compound, as 

 we had previously inferred, we next proceeded to make some of 

 these derivatives, and redetermine their properties. In this work, 

 the more easily purified parachlorbenzylbromide was used instead of 

 the chloride. 



Parachlorbenzylalcohol, G^H^CIGH^OH, was made by boiling the 

 bromide (or chloride) with water in a flask with a return-cooler. The 

 formation of hydrobromic (or hydrochloric) acid by this reaction was 

 proved by testing the water, which had become acid, with argentic 

 oxide, when argentic bromide (or chloride) was formed, and the acid 

 reaction disappeared. The alcohol was made also from the acetate 

 by boiling with water : sealing with aqueous ammonia, as recom- 

 mended by Beilstein and Kuhlberg, being found in this case un- 

 necessary : it was purified by crystallization from boiling water, dried 

 in vacuo, and analyzed. 



