Ryan and Shannon — The Condensation of Aldehydes^ Sfc. 327 



solidified in the receiver as glistening, colourless plates, which melted at 

 48° C, and dissolved in the ordinary organic solvents. It gave on analysis : 



0-1437 substance gave 0-4377 COg and 0-1141 H2O, 

 corresponding to 83-09 H 8-82. 

 Oj^HigO requires C 8316 H 8-91. 



Its oxime, which was obtained in the usual manner, crystallised from 



carbon tetrachloride as colourless needles, melting at 108-109° C, and it gave 



on analysis : — 



0-1894 grams substance gave 10-4 c.c. moist nitrogen at 17-5° C. and 



745 m.m. 



corresponding to jST 6-3. 



C^^HjglSrO requires N 6-45. 



C. — Action of Aldehydes on Butyl- Acetone in the Presence of 

 Hydrochloric Acid. 



1. ylction of Piperoncd. 



Piperonal (21 grams) was dissolved in alcohol, saturated with anhydrous 

 hydrochloric acid at - 5° C, and butyl-acetone (58 grams), prepared from 

 butyl-acetoacetic ester, was added. The mixture, which was contained in a 

 tightly-stoppered fiask, turned purple in colour, and was allowed to remain 

 in a freezing mixture for four days. The flask then contained a tarry liquid, 

 together with a solid. The hydrochloric acid was allowed to evaporate, and 

 by repeated crystallisation from hot alcohol, aj'ellowish solid was finally 

 obtained. This solid separated from hot methyl-ethyl ketone as small, 

 colourless prisms, melting at 237-239° C, soluble in acetone or chloroform, 

 and very sparingly soluble in methyl alcohol, ether, or acetic ester. It gave 

 on analysis the following results : — • 



0-1288 substance gave 0-3431 COg and 0-0622 HgO, 

 corresponding to C 72-65 H 5-36. 

 C3, H.,g07 requires C 72-94 H 5-09. 



Apparently the substance was formed in accordance with the equation: 



CH3 . CO . CH2 . C.Hg + 3CgH3 (O2CH2) . CHO = G,,U.^fi, + SR^. 



2. Action of Benzaldehyde. 

 A saturated solution of alcoholic hydrochloric acid was cooled to - 10° C, 

 and to it 7 grams of butyl-acetone and 18 grams of benzaldehyde were 

 added. After remaining four days in a freezing mixture, the tar which had 



