On the Synthesis of Hydrocarbons of the Benzole Series. 311 



was readily identified as benzoic acid, the formation of which 

 takes place as follows : — 



€ 7 H 5 0Cl + H 2 0=e 7 H 6 O 2 + HCl. 



Chloride of Benzoic 



benzoyle. acid. 



Tollens and Fittig* have described the synthesis of a number 

 of hydrocarbons of the benzole series. It is an extension of 

 Wurtz' s method of obtaining in the fatty-acid series, the mixed 

 radicals by the union of two different alcohol radicals. 



When to a mixture of monobromobenzolet and iodide of me- 

 thyle and ether sodium was added, a brisk reaction was established 

 which had to be moderated. After distilling off the ether at 

 60°, almost the entire quantity passed over between 108° and 

 116°, and, after one or two rectifications over sodium, was found 

 to boil at 111°. This substance has the composition of methyl- 



phenyle, € 7 H 8 = ^ tt 3 >. It is a colourless liquid, resembling 



benzole in its odour, and with the specific gravity 0*881 . It 

 resembles in all respects the toluole from coal-tar, not merely 

 in its physical but in its chemical properties ; for the authors 

 have easily obtained from methyl-phenyle the derivatives cha- 

 racteristic of toluole, nitrotoluole, and toluidine; like toluole, 

 too, it yields benzoic acid by oxidation ; so that there is no doubt 

 as to the identity of the two substances. 



By treating a mixture of iodide of ethyle and bromobenzole 

 with sodium, Tollens and Fittig obtained the mixed radical 



ethyl-phenyle, ^m V, which has the same composition as 



xylole. It forms a nitro-compound, Q 8 H 9 (NO 2 ), which, when 

 reduced, yields a crystallizable base. 



In like manner a mixture of bromobenzole and bromide of 



amyle yields a mixed radical, amyl-phenyle, ns jjii f • It boils 



at 195°, and forms, when treated with fuming nitric acid, a nitro- 

 compound, € n H 15 (N0) 2 . By oxidation with a concentrated 

 solution of chromic acid, it yields a mixture of acids difficult to 

 separate, the greater part of which is benzoic acid, 



Berthelot and De Luca, by treating iodide of allyle with sodium^ 

 obtained a new hydrocarbon, G 3 H 5 , which they called allyle. 

 Wurtz has made an extended series of investigations, of which 

 this substance is the starting-point J. According to Wurtz, its 



* Liebig's Annalen, September 1864. 

 t Phil. Mag. vol. xxv. p. 218. 

 X 'Repertoire de Chimie, 1864. 



