Ryan and Dunlea — On Unsaturated fi-Diketones. — I. 7 



ether, or chloroform. Its alcoholic solution gives no colouration with ferric 

 chloride. 



Cinnamyl-propionyl-methane C 6 H 5 CH : CH . CO . CH 2 . CO . CH 2 CH 3 . 



59 grms. of methyl cinnamate were dissolved in 27 grms. of ethyl-methyl- 

 ketone, and 8'8 grms. of sodium wire were added under the same conditions 

 as in the previous condensations. 



When the aqueous extract was treated with carbon dioxide, only a small 

 amount of oily matter separated (which in alcoholic solution gave a dark- 

 brown colouration with ferric chloride, and may be the enol form of the above 

 diketone). Subsequent acidification with acetic or hydrochloric acid pre- 

 cipitated a crystalline mass, which was filtered on the pump, washed with 

 water, and recrystallized from dilute alcohol. The crystals, when heated, begin 

 to give off a vapour at 130° C. The residue softens at 154° O, and melts to a 

 yellow liquid about 161-163° C. 



0-2310 substance gave 0-6551 C0 2 , and 0-1482 H 2 0, 

 corresponding to C 77-3, H 71. 

 C 13 H u 2 requires C 77"2, H 6-9. 



Cinnaniyl-propionyl-rnethane crystallizes in small prisms, easily soluble 

 in alcohol, much less so in ether or chloroform, almost insoluble in ligroin. 

 Its alcoholic solution yields no colouration with ferric chloride. The diketone 

 is soluble in potash, and can be reprecipitated by addition of acids. The 

 crystals yield no colouration with concentrated sulphuric, but dissolve in it 

 to a colourless solution. 



Cinnamyl-isofaityryl-methane, 



/CH 3 

 C 6 H 5 CH : CH . CO . CH 2 . CO , CH 



\CH 3 



28 grammes of cinnamic methylester were dissolved in 15 grammes of 

 methyl-isopropyl-ketone and 5 grammes of metallic sodium added under 

 conditions similar to those described in the foregoing condensations. From 

 the alkaline extract carbon dioxide precipitated only a small quantity of oily 

 matter whose alcoholic solution gave a red colour with ferric chloride. When 

 the oil had been removed by ether, acidification of the aqueous residue yielded 

 a precipitate which was filtered off and recrystallized from alcohol. When 

 heated the crystals emit a vapour at 145° ; the residue softens at 165 and 

 melts to a yellow liquid at 173-175° C 



0-3020 substance gave 0-8595 C0 2 and 0-2030 H 2 0, 



corresponding to C 77-6 H 7"4 



C»H 19 0, requires C 777 H 75 



