58 Proceedings of the Royal Irish Academy. 



With the mono sodium derivative of the latter they condensed cinnamic 

 chloride, thus obtaining dieinnainoyl-acetyl-methane, which on hydrolysis 

 yielded dieinnamoyl-methane : — 



C 5 H 5 . CH : CH . CO . CHN'a . CO . CH 3 + CI . CO . CH : CH . Gft 



= C,H 5 . CH : CH . CO . CH . CO . CH : CH . C.H ; - XaCl 

 / CO 

 / CH, 

 / H.O 



C t H s . CH : CH . CO . CH : . CO . CH : CH . C. : H. - CH 3 . COOH. 



The synthesis of a derivative of dieinnamoyl-methane was also tried by 

 us by the second method mentioned above; and with the results of these 

 experiments the present paper is concerned. 



Although the study of the two methods was carried on simultaneously, 

 unforeseen difficulties prevented the publication of the results of the second 

 method. In the interval there has appeared another paper on similar bines 

 by Heller [Ber. 47 (1914), p. 887], in which a claim is put forward for the 

 synthesis of a stereo-isomeride of curcumin, which he calls iso-curcumin. 



(CH 3 0) (HO) CJ3.; . CH : CH . CO . CH, . CO . CH : CH . C 6 H, (OH (OCH,b 



This substance according to Heller is formed by the condensation of 

 vanillin with acetylacetone in the presence of alcohohc hydrochloric acid 

 thus : — 



CO.CH 3 CO.CH:CH.C c H 3 <OH)(OCH 



/ / 



<JH, - 20HC.C,H,(OH)(OCH^ = CH, - 2H,0. 



\ \ 



CO. CH, CO.CH:CH.C 6 H 3 (OH)(OCH,) 



Making all allowances for the necessary imperfection of a preliminary 

 report, Heller's paper is not convincing. We have found that the first 

 product of the action of benzaldehyde on acetylacetone is not 



C 6 H 5 CH : CH . CO . CH, . CO . CH„ 



a crystalline compound obtained in another way by us [loe. cit., p. 4] and 

 melting at S3-84" C, but rather a chlorinated substance, which, when heated 

 in vacuo [Knoevenagel Ann. 231, p. 80], forms an oily compound 



CH, . CO . C . CO . CH, 

 CH 



C 6 Hi. 



Consequently the result of complete interaction of vanillin with acetyl- 



