Ryan and Algau — Studies in the Diflavone Group. 19 J 



with water and alcohol. A solution of the solid in hot chloroform was 

 washed with water, concentrated and mixed with alcohol. The yellow solid 

 which separated was re-crystallized from chloroform, and dried at"105° C. for 

 analysis :— 



0-1475 substance gave 0-3930 C0 2 and 0-0603 H,0 

 corresponding to C 72'66 H 4-54 

 C> 6 H, 5 0c, requires C 7321 H 4-25. 



Dianisylidene-dicoumaranone crystallizes from chloroform in yellow prisms, 

 which after drying at 150° C, melt at 327°-328-5° C. 



It is almost insoluble in the usual organic solvents. 



The crystals dissolve in concentrated sulphuric acid, forming a deep 

 purple-red solution. 



In a similar manner, the same dianisylidene-dicoumaranone was obtained 

 from j3-dianisylidene-diacetoresorcinol. 



C. Derivatives of Diflavanone. 



7. Anisylidene-%-p. methoxycinnamoyl-3-hydroxy-l^-methoxyfMvanone (IX). 







HO /^/^ CH . C 6 H 4 . OCH 3 

 CH 3 . C 6 H 4 . CH : CH • CO \/\/ C : CH . C 6 H 4 . OCH 3 



CO 



Diacetoresorcinol (5 grams) and anisaldehyde (20 c.cs.) were dissolved in 

 200 c.cs. of hot alcohol, and dry hydrochloric acid was passed into the solution 

 until the latter was saturated. The mixture was allowed to stand, with 

 occasional heating for several days in a stoppered flask. The dark-red, oily 

 product which was precipitated, was crystallized several times from a mixture 

 of chloroform and alcohol. By this means orange-yellow crystals were 

 obtained, which gave on analysis the following results : — 



0-1556 substance gave 0-4246 C0 2 and 0-0704 H,() 

 corresponding to C 74-42 H 5 - 02 

 C 34 H 27 7 requires C 74-45 H 5-1. 



Anisylidene-8-p. methoxycinnam,oyl-3-hydroxy-!/-methoxyflavanone crystal- 

 lizes from a mixture of chloroform and alcohol in orange-yellow leaves, which 

 melt at 243°-245° C, are soluble in chloroform, slightly soluble in benzene, 

 and almost insoluble in alcohol. 



The crystals dissolve in concentrated sulphuric acid, forming a deep-blue 

 solution, the colour of which rapidly changes to a purple-red. 



