DiiUMM, ]\1acMahon, and Rvan — The Constitution of Ca lochia. lo;i 



xxix, p. 2417), were added. A current of dry hydrogen chloride was passed 

 through tlie ethereal soliiliou until (after about an hour) crystals of the 

 ketimide hydrochloride no longer separated. The contents of the Hask were 

 filtered and the solid was washed with 30 c.c. of etlier. It was tlien dissolved 

 in 400 c.c. of water, previously heated Lo 30-40'^ C, and 60 c.c. of 30 percent, 

 sulphuric acid were added. The sulphate, which separated as a felted mass 

 of colourless needles, was filtered and boiled for half an hour wiLh 500 c.c. of 

 water to which a few grams of potassium acetate had been added. On 

 allowing the solution to cool slowly 38 g. of 3-5-dihydroxycoumaranone 

 separated. 'J'he properties of the substance agreed with those described by 

 Sonn (Ber. Dtsch. Cheni. Ges., 1917, 1, p. 1262), who has already prepared the 

 substance by this method. 



2. o'5-JJimcthoxi/coumifranone. 

 A concentrated aqueous solution of potash was allowed to drop slowly into 

 a mixture of 38 g. of 35-dihydroxycoumaranone and 100 c.c. of water until 

 the coumaranone had just dissolved; 85 c.c. of dimethyl sulphate were then 

 added. The mixture was kept faintly alkaline and well shaken while tlie 

 dimethyl sulphate was being added. The methylated product was filtered 

 and dissolved in 60-70 c.c. of boiling glacial acetic acid which was then 

 cooled and filtered. By diluting the filtrate with three times its volume of 

 water a greyish-white precipitate was obtained. The precipitate was 

 recrystallised first from alcohol, and afterwards from boiling water with 

 addition of a little decolorising charcoal. About 15 g. of diinethoxycoii- 

 maranone were obtained as colourless acicular crystals which melted at 

 136-138" C, and gave on analysis the following residts: — 



0'2060 substance gave 0'4676 CO. and 0"0946 H2O, corresponding to 

 .C 61-i), H 5-10. 



C,oH,„04 requires C 61-83, H 5-19. 



3. Vcratri/lidene-o'o-dimcthoxycmimccranonc. 

 A mixture of 5 g. of 3'O-dimethoxycoimiaranone, 4'5 g. of veratric aldehyOe, 

 50 c.c. of alcohol and 20 c.c. of hydrochloric acid (sp. g. 1'14) was heated 

 under a reflux condenser for ten minutes, and was then allowed to remain 

 forty-eight hours at the room temperature. A crystalline solid separated. 

 I'his was filtered and recrystallised successively from glacial acetic acid, 

 alcohol, and ligroin. The pure substance weighed 6 g., and gave on analysis 

 the following results : — 



0-1790 substance gave 0-4366 CO, and 0-0882 H^O. 



0-1425 „ „ 0-3470 CO2 and 0-0672 HoO, corresponding to 



C 66-53, 66-38, H 5-47, 5-23. 

 CigU^gOg requires 66-63, 11 5-30. 



K.l.A. Vr.OC, VOL. XXXVI, SECT. B. [A'] 



