Ryan and Devink — Condensation of Aldehydes with Ketones. 213 



that got by Harries and Muller, we prepared its oxime, and found that it 

 also melts at 195°-196° C. 



An alcoholic solution of 2 grams of the condensation product melting 

 at 81°-83° C, and 2 grams of hydroxylamine hydrochloride, was mixed 

 with a saturated aqueous solution of 1*5 grams of sodium carbonate, and 

 the mixture was heated to gentle boiling for several hours under a reflux 

 condenser. The colourless, crystalline precipitate which formed was filtered, 

 washed with water, dried, and recrystallized from chloroform and alcohol. 



When dried at 110° C, it melted at 195°-196° C, and gave on analysis the 

 following results : — 



0-1229 substance gave 0-3452 C0 2 and 0'0752 H 2 

 corresponding to C 76'66, H 6 - 8 

 C, 9 H l8 ONOH requires C 76-87, H 6-76. 



The oxime crystallizes in needles which are sparingly soluble in alcohol, 

 and soluble in chloroform, ether, or benzene. 



The phenylhydrazone, of the compound, which melts at 81°-83°C., was 

 prepared by dissolving 1*5 grams of the condensation-product and 1 gram of 

 phenylhydrazine in 20 c.cs. of absolute alcohol (warm), and letting the mixture 

 stand with occasional warming for a few days. The phenylhydrazone was 

 filtered and washed with alcohol. When dried it melted at 134° C, and 

 gave on analysis the following results :— 



0-1362 substance gave 9 - 4 c.cs. of moist nitrogen at 19° C. and 758 m.m.p. 

 corresponding to N 7'9 

 C 18 H 19 : N • NH . C 6 H 5 requires N 7"9. 



It crystallizes in short colourless needles, which slowly acquire a light- 

 brownish colour on exposure to light. 



Semi-carlazone of the compound melting at 81°-83° C. 



A solution of 1.5 grams of semi-earbazide hydrochloride and an equal 

 weight of anhydrous sodium acetate in a little water was added to an alcoholic 

 solution of 2-6 grams of the compound melting at 81°-83° C. The mixture 

 was allowed to stand for two days in a warm place, then heated to boiling, 

 and filtered. After washing with water and alcohol it crystallized from a 

 mixture of chloroform and hot alcohol in fine needles, which were filtered 

 and washed with ether. When dried at 110° C, it melted at 195°-198° C, and 

 gave on analysis the following results : — 



- 1857 substance gave 20-2 c.cs. of moist nitrogen at 15° C. and 757 m.ra. p. 

 0-1392 substance gave 0-3590 C0 2 and 0-0839 H 2 

 corresponding to C 70-3, H 6-7, N 127 

 C le H, 9 : N . NH . CO . NH, requires C 70-6, H 6'5, N 12'7. 



