202 PROCEEDINGS OF THE AMERICAN ACADEMY 



VII. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 

 HARVARD COLLEGE. 



RESEARCHES ON THE SUBSTITUTED BENZYL COM- 



POUNDS. 



SIXTH TAPER. 



THE ACTION OF BROMINE ON TOLUOL AND SOME OF ITS 

 DERIVATIVES. 



By C. Lorino Jackson and A. W. Field. 



Presented June 12, 1878. 



The history of the action of halogens on toluol begins with the dis- 

 covery of toluol by Pelletier and Walter, who say in their paper,* 

 published in 1838, on " retinnaphte " (toluol) from coal tar, that by 

 distilling it repeatedly in a stream of chlorine there was formed a 

 brownish-yellow oil with a sharp taste, a very strong smell somewhat 

 like that of horse-radish, and a powerful action on the eyes, whose 

 formula, founded on a doubtful analysis, was C.H C C1 2 , and which with 

 potassic hydrate gave jiotassic chloride and an oil with a different 

 smell. They also tried the action of bromine on boiling retinnaphte, 

 and made in this way a compound similar to the preceding in every 

 respect, but they observed that the cold hydrocarbon was apparently 

 unaffected by chlorine. 



Devillef was the next to take up the subject in 1841, in his paper 

 on balsam of tolu, from which he obtained a hydrocarbon (benzoene) 

 identical with the retinnaphte of Pelletier and Walter. From this 

 he made the following compounds: C.H. CI, boiling-point 170°, by the 

 action of chlorine on the hydrocarbon when cooled and protected from 

 light; C-II..C1, in diffused daylight: C.IICl- when the chlorine was 

 in excess ; C 7 H G C1 8 in direct sunlight; and C r II 2 Cl G by repeated dis- 

 tillation in an atmosphere of chlorine. 



* Ann. Cliim. Phys., lxvii. 209. t Ibid., ser. 3, iii. 178. 



