1869.] 



Action of Bromine vpon Ethylbenzol. 



129 



This substance, from its characteristic aromatic odour and from the 

 following analyses, was identified as the styrolyl-ether already described. 



0*2523 grm. substance gave 0*7358 grm. carbonic anhydride and 0*2 1 19 

 water. 



0*1993 grm. substance gave 0*5829 grm. carbonic anhydride and 0*1666 

 grm. water. 



Calculated. Found. 



C 10 120 80*00 79*54 79*75 



H u 14 9*36 9*33 9*30 



0 16 



The simultaneous production of this body and of the ethyl acetate may 

 be thus represented : — 



C 6 H 6 {C 2 H 4 Br + ° 2 j£ ° } O + 2^ C ^ } O 



= C 6 H 5 { C 2 H 4 -0-C 2 H 5 + } 0 + KBr + H a O. 



The remainder of the distillate consisted principally of the acetic ether, 

 C 6 H.{C 2 H 4 — O — C 2 H 3 O. This body is a sweet-smelling liquid, possess- 

 ing the characteristic fragrant odour of the acetic ethers and boiling at 

 217°-220°. The quantity produced, however, was so small as to preclude 

 further investigation, or any attempt to prepare the alcohol. 



Fittig has recently obtained phenylpropionic acid (hydrocinnamic acid), 

 C 6 H 5 {CH 2 — CH 2 — COHO, by acting upon chlorinated ethylbenzol by 

 means of potassium cyanide and treating the resultant cyanide with potash . 



C 6 H 5 {CH 2 - CH 2 CN+ 2H 2 0 = C 6 H 5 {CH 2 -CH 2 - COHO + NH 3 . 



I have attempted to repeat this reaction with the bromide obtained by 

 treating ethylbenzol with bromine free from iodine, but without success, 

 although the experiment has been frequently made under the exact con- 

 ditions described by Fittig. So easily, according to Fittig, is the transfor- 

 mation effected, that this chemist has recommended the reaction as afford- 

 ing the best method of obtaining phenylpropionic acid. I am unable to 

 discover any reason for the discrepancy in the results of our observations. 

 It is certainly very remarkable that the reaction should occur in the case 

 of the chloride and not in that of the bromide. 



The experiments which led to the discovery of the above method of 

 effecting the substitution of hydrogen in the phenyl or in the lateral group 

 at will had for their object the preparation by synthesis of ethylbenzoic acid 

 from the bromide, C 6 H 4 Br{C 2 H.. It therefore became interesting to 

 trace the reaction which occurs on submitting the new bromide to a similar 

 treatment. A small quantity (about 7 grms.) of the bromide was mixed 

 with about five times its volume of anhydrous ether, and a large excess of 

 sodium cut into slices as thin as possible added, and a slow continuous 



