Ryan and O'Neill — Studies in the Diflavone Group. 181 



When dried at 105° C, it melted at 142-143° C, and gave the following 

 results on analysis : — 



0-2108 substance gave 0-5585 C0 3 and 0-1044 H 2 0, 

 corresponding to C 72-2 H 5 - 5. 



CHmO, requires C 722 H 5-5. 



Anisylidene — 3.4.4' trimethoxy-flavanone crystallizes from alcohol in nearly 

 colourless prisms, which are sparingly soluble in cold, and readily in hot, 

 alcohol, sparingly soluble in ether, soluble in carbon disulphide, and very 

 soluble in benzene or chloroform. 



Its solution in warm alcohol gave no coloration with ferric chloride. 

 The crystals turned a dark red colour on contact with concentrated 

 sulphuric acid, in which they dissolved to a red solution. 



11. Piperonylidene-oA. dimethoxy-B' A' . methylenedioxy-flavanone. 





OCH 







CHO 

 5 



-C' C CHCH-0 



1 XI || | " 2 



=CH 

 2 







CHC 6 H 3 = 



°r c 



Piperonal i*eacts with gallacetophenone-dimethylether in the presence of 

 alcoholic hydrochloric acid to form a mixture of piperonylidene-3.4. dimethoxy- 

 3'.4'.methylenedioxy-flavanoneaudpiperonylidene-gallacetophenone-dimethyl- 

 ether. The flavanone derivative being less soluble in a mixture of chloroform 

 and alcohol than the chalkone, was separated from the latter by recrystalliza- 

 tion. It was obtained in the form of colourless crystals, which melted at 

 184-186° C, and gave on analysis the following results : — 



0-1198 substance gave 0-2957 C0 3 and 0-0441 H 2 0, 

 corresponding to C 67'3 H41, 



C 36 H M O s requires C 678 H43. 



Piperonylidene-3 . 4 . dimethoxy-B' . 4'. methylenedioxy-flavanone crystallizes 

 from boiling alcohol in colourless needles, which are sparingly soluble in 

 ether, soluble in benzene, and very soluble in chloroform. 



Its solution in boiling alcohol gave no coloration with ferric chloride. 



The crystals dissolve in concentrated sulphuric acid, forming a cherry-red 

 solution. 



12. Piperonylidene-gallacetophenone-diniethylether. 



OCH 



J:^ .oh 



CHO C-r ^C^ 



3 I XII || 



CH^ ^co-ch=ch-chOCH 

 e j V 2 



(a) Piperonylidene-gallacetophenone-dimethylether is formed as an inter- 



