OF ARTS AND SCIENCES. 209 



XVIII. 



CONTllIBUTIONS FROM THE CHEAOCAL LABORATORY 

 OF HARVARD COLLEGE. 



RESEARCHES ON THE SUBSTITUTED BENZYL COM- 

 POUNDS. 



By C. Lorixg Jacksox. 



Presented, June 14th, 1S76. 

 INTRODUCTION. 



The existence of the benzyl compounds was first established by 

 Cannizaro,* in 1853 ; for, although Liebig and Wohler.t in their clas- 

 sical research on the benzoyl compounds, obtained benzylalcohol as a 

 secondary product from the action of ^lotassic hydrate on benzaldehyd, 

 they merely spoke of it as an oily liquid, and did not determine its 

 composition or properties. It was also Cannizaro t who, in 1855, 

 showed that toluol, when treated with chlorine, yielded a substance 

 identical with the benzylchloride prepared fi-om benzylalcohol by 

 means of hydrochloric acid. The nature of the action of chlorine on 

 toluol was not, however, thoroughly understood until Beilsteia and 

 Geituer,§ in 1866, found that chlorine converted cold toluol into chlor- 

 toluol, while, with boiling toluol, it yielded benzylchloride. In the 

 same paper, they predicted that pure chlorbenzylchloride could be pre- 

 pared by the action of chlorine, either on hot chlortoluol or on cold ben- 

 zylchloride. Both these methods were tried successfully by Neuhof || in 

 the same year, but the chlorbenzylchloride thus obtained was not the 

 first substituted benzyl compound known, as Beilstein ^ had already 

 obtained the chlorbenzylmercaptan, and Naquet** the chlorbenzyle- 

 thylether, from the mixture of dichlortoluols, made by acting upon toluol 



* Ann. Chem. Pharni., 88, p. 129. 

 t lb., 3, p. 249. 

 t lb., 96, p. 246. 



§ Beilstein and Geitner, Ann. Chem. Pharm., 139, p. 331. 

 11 Neuhof, Zeitschr. der Chem., '66, p. 653. 

 T Beilstein, Ann. Chem. Pharm., 116, p. 346. 

 ** Naquet, ib., Sup. 2, p. 250. Comptes Rend., 56, p, 129. 



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