002 J. READ AND M. M. WILLIAMS. 



These results having been obtained by using a suspension 

 of cinnamic acid in water, it was next of interest to inves- 

 tigate the action of the reagent upon a neutral solution of 

 a soluble salt of the acid ; for this purpose the cinnamic 

 acid was dissolved in the minimum amount of sodium 

 bicarbonate solution. Upon conducting the operation in 

 the manner described above, the bromine was absorbed 

 more rapidly than under the original conditions ; and a 

 heavy oil, accompanied by a small amount of crystalline 

 material, separated from the solution. At the end of the 

 reaction, a little dilute sulphuric acid was added to the 

 liquid; the oil was extracted with light petroleum and 

 identified as /?-bromostyrolene; the accompanying insoluble 

 solid product proved to consist essentially of cinnamic acid 

 dibromide. A third product, namely, phenyl-a-bromolactic 

 acid, was extracted from the aqueous solution in the usual 

 way by means of ether. 



In this way, 20 grams of cinnamic acid yielded 18*7 grams 

 of phenyl-a-bromolactic acid, 1*9 grams of cinnamic acid 

 dibromide, and 10*5 grams of /3-bromostyrolene. Thus, the 

 relative percentage amounts of cinnamic acid converted to 

 bromohydrin, dibromide, and /3-bromostyrolene were 52*8, 

 4*6, and 42*6, respectively. The amount of bromine used 

 was 21*3 grams; and an examination of the above figures 

 shows that both the cinnamic acid and the bromine are 

 quantitatively accounted for. 



The interesting result is thus revealed that by modifying 

 the conditions of the reaction in this simple manner the 

 yield of bromohydrin falls from 82*9 to 52*8 per cent., the 

 yield of dibromide falls from 17*4 to 4*6 per cent., and a 

 new product, /3-bromostyrolene, is formed to the extent of 

 42*6 per cent. The last named substance being evidently 

 derived by decomposition of the sodium salt of cinnamic 



