OP ARTS AND SCIENCES. 2'Al 



SECOND PAPER. 



ON PARABROMBENZYL COMPOUNDS. 

 Woodbury Lowery. 



Parahromhenzylalcohol^ C^JI^Br CB., Off.) — This substance was most 

 easily prepared by boiling jjarabrorabenzylbromide with water, in a 

 flask with a return-cooler, for two or three days, until it no longer at- 

 tacked the eyes. The reaction ran as follows : C^H^BrCH^Br-l-H^O 

 =:CgH^BrCH.,OH-j- HBr. The presence of the hydrobromic acid 

 was established by treating the acid aqueous filtrate with argentic oxide, 

 when argentic bromide was formed, and the solution became neutral. 

 This method is analogous to that employed by Grimaux * for convert- 

 ing tollylenebromide into tollyleneglycole, except that Grimaux heated 

 the haloid compound with water at 170° to 180'^, while I obtained the 

 alcohol by boiling in a flask with a reverse-cooler. The action of 

 water on benzylchloride at high temperatures has been very thoroughly 

 studied : the first research in this field having been undertaken by 

 Limprichtf as early as 1866, who by heating the two substances to 

 190° obtained anthracene, a hydrocarbon Cj^Hj^, later identified by 

 Van Dorp t as benzyltoluol, and beuzylether, which he supposed was 

 formed from benzylalcohol ; but neither he, nor Van Dorji, nor 

 Zincke, § who afterward made out the theory of this reaction, men- 

 tioned obtaining benzylalcohol in this way. The alcohol was also 

 obtained in the ordinary way by heating parabrombenzylacetate with 

 aqueous ammonia in a sealed tube to 160*^. The alcohol in whichever 

 way prepared was 25urified by crystallization from boiling watei', and 

 its composition established by the following combustion : — 



Required for C.HeBr.OH. Pound. 



Carbon 44.92 44.94 



Hydrogen 3.74 3.99 



Properties. — It forms long elastic transparent colorless flattened 

 needles, with a brilliant pearly lustre and a disagreeable odor; its vapor 

 does not attack the eyes. Melting-point, 69°. It burns with a lumi- 

 nous green-bordered flame, distils with steam although slowly, and is 

 very slightly soluble in cold, more freely in boiling water, easily soluble 

 in alcohol, ether, benzole, and carbonic disulphide. 



* Grimaux, Comptes Rend., 70, p. 1363; Ann. Chem. Pharra., 155, p. 338. 



t Limpricht, Ann. Chem. Pharm., 139, 303. 



X Van Dorp, ib., 169, 207. 



§ Zincke, Ber. D. Cli. G., 1874, 276. 



