Ryan and Algar — Studies in the Diflavone Group. 187 



tive such as (I), which is afterwards converted by the alcoholic hydrochloric 

 acid into a derivative of diflavanone (IV). 



o 



CH 3 . C 6 BU • CH /\/\/\ CH . C 6 H 4 . OCH 3 



H 2 C ^/^/'x/ 1 CH* 

 CO CO 



By further condensation with anisaldehyde the latter compound forms 

 dianisyliclene-4'.4'-diniethoxy-diflavanone (X). 



Experimental Pakt. 



A. Derivatives of Dichalkone. 



1 . Bianisylidene-diacetoresorcinol-dimethylether (V). 



CH3O /\ OCH3 

 CH3O . C 6 H 4 . CH : CH . CO \ ) CO . CH : CH . C 6 H 4 . 0CH 3 



Two grams of diacetoresorcinol-dimethylether were dissolved in 25 c.cs. 

 of hot absolute alcohol and 4 c.cs. of anisaldehyde were added. To the warm 

 solution 2 c.cs. of 25 per cent, sodium hydrate were added, and the mixture 

 was heated on a water-bath until, after a few minutes, a yellow solid separated. 

 The solid was filtered, washed first with alcohol, next with water, dried, and 

 finally recrystallized from a mixture of chloroform and alcohol. 



The yield was nearly quantitative. 



The substance, when dried at 105° C, melted at 204-205° C, and gave on 

 analysis the following results ; — 



01553 substance gave 0-4176 CO, and 0-0804 H 2 

 corresponding to C 73'34, H 5'75 

 C 29 H 26 6 requires 73-36, H 5-68 



Dwnisylideiie-diacetoresorcviwl-dimethylether crystallizes from benzene in 

 light yellow, long needles, which are insoluble in petroleum ether, nearly 

 insoluble in cold alcohol, sparingly soluble in cold chloroform or benzene, and 

 dissolve more readily in the latter solvents on warming. 



The crystals are coloured red by concentrated sulphuric acid, in which they 

 dissolve to a red solution. 



A solution of the substance in hot alcohol gives no coloration with ferric 

 chloride. 



An attempt was made to demethylate the compound by heating it with 

 concentrated hydriodic acid, but the product was so resinified that no crystal- 

 line compound could be isolated from it. Similarly, demethylation by means 

 of anhydrous aluminium chloride in boiling xylene gave unsatisfactory results. 



[2E2] 



