'2 { J'2 Proceedings of the Royal Irish Academy. 



Experimental Pap.t. 

 1. Yer -atr ylidene- Acetone. 



Yeratrie aldehyde was prepared by addiDg 37 - 5 grams of hot 50 per cent, 

 aqueous potash to a solution of 25 grams of vanillin and 41-5 grams of 

 dimethyl sulphate in a little alcohol (vonKostanecki and J. Tambor Ber. xxxix 

 (1906). p. 4022). When the energetic reaction had subsided, water was 

 added, the mixture was made slightly alkaline and the veratric aldehyde was 

 extracted with ether. After evaporation of the ether, colourless crystals of 

 veratric aldehyde were obtained. 



The yield was nearly quantitative. 



To a solution of 25 grams of veratric aldehyde in a mixture of 96 c.cs of 

 acetone and 34 c.cs of water 3*4 c.cs of 25 per cent, sodium hydrate were 

 added. The mixture was left for twelve hours in a stoppered flask, and then, 

 after addition of 150 c.cs of water, the solid was extracted with ether. The 

 vera try lidene-ace tone, which was obtained after removal of the ether, was 

 recrystallized from hot, dilute alcohoL It melted at S5°-S6~ C, and gave on 

 analysis the following results : — 



0T006 substance gave 0-2582 C0 2 and 0-0606 H 2 

 corresponding to C 69 - 99, H 6 - 68 

 C„H u O, requires C 6990, H 6.79. 



Vcratrylident-aatont crystallizes from dilute alcohol in almost colourless 

 prisms, which are readily soluble in alcohol, ether, chloroform, or benzene. 



Its alcoholic solution gives no coloration with ferric chloride. 



The crystals are coloured red on contact with concentrated sulphuric acid 

 in which they dissolve, forming an orange-coloured solution. 



Yeratrylidene-acetone was also obtained by methylating ferulic-methyl- 

 ketone, the latter substance having been prepared by condensing vanillin 

 with acetone in the presence of dilute alkali 



Ferulic-methylketone (15 grams) and methyl iodide (22 grams) were 

 dissolved in 200 c.cs of alcohol, and 8*74 grams of 50 per cent, aqueous potash 

 were added. The mixture was heated to gentle boiling under a reflux 

 condenser for two and a half hours. The alcohol was distilled, water was 

 added, and the ketone was extracted with ether from the alkaline solution. 

 When the oily residue, which remained after evaporation of the ether, was 

 covered with a layer of alcohol, it became crystalline. After recrystallization 

 from dilute alcohol it melted at 85"-86 s C. 



L. Francesconi and G. Cusmano ((razz. chim. ital. xxxviii '1908), II, p. 70) 

 by a similar method obtained yellow acicular crystals, which melted at 

 168' C, and which apparently constitute an isomeric form of the compound 

 described above. 



