DiiUMM, MacMahon, and Ryan — The Consliiulion oj Cidecliin. 151 



prepared by Friedlaender and Schnell (Ber. Disch. Chem. Ges., 1897, 

 XXX, p. 2153) from oi-chloroiDhloracetopheiione-dimelhylether. It was prepared 

 by us by the more convenient method of Sonii (ibid., 1917, 1, p. 1262-70] 

 from pldoroghicinol and chloraeetonitrile. 



Veratric aldehyde in the presence of alcoholic hydrochloric acid condensed 

 with dimethoxycouniaranone forming veratrylideue-o-5-dimethoxyconniar- 

 anone (vi). 



O ^^OCH 



■iC = CH— < 



3 

 OCH, 



CO 



OCH, 



VI. 



When this substance was reduced by hydrogen in the presence of platinum 

 black diliydro-Aeratrylideiie-dimethoxycoumaranone was obtained, and since 

 the addition of the hydrogen apparently takes place at the double bond, the 

 formula of the substance is represented by Tii 



-Ha-( \ 



.OCH, 



3 



OCH, 



CO 



OCH, 



VII. 



On further reduction, this substance (vii) should yield successively Yin and 

 IX — possibly deoxycatechin-tetramethylether (below) may be represented by 

 the formula ix. 



OCH 



OCH, 



CH— CH- 



CHOH 



VIII. 



■o° 



CH, 



OCM, 



CKO 



OCH, 



IX. 



Deoxycatechin-tetraniethyletlier, which melts at 13(3-137'^ C, was itself 

 obtained by the reduction of dehydrocatechin-telrameihylether by means of 

 hydrogen and platinum black. 



Further e.xperimenls will be made with I he object of preparing the 

 substances viil and IX. 



