JACKSON AND GRINDLEY. ACETALS FROM QUINONES. 425 



clilordiphenoxydroquinone even when hot. It dissolves in alkalies and 

 is reprecipitated from the solution by acids. On long standing or 

 boilino- with sodic hydrate it is saponified, giving the sodium salt of 

 chloranilic acid which separates in long dark carmine red needles. 



By the action of oxidizing agents, such as ferric chloride, dilute 

 nitric acid, or potassic dichromate in acid solution, it is easily changed 

 to the corresponding quiuone. 



Action of Aniline on Dichlurdiphenoxyqidnone. 



The dichlordiphenoxyquinone was treated with aniline in the expec- 

 tation of removing the two remaining atoms of chlorine. For this 

 purpose 1 gram of dichlordiphenoxyquinone was mixed with 5 grams 

 of aniline, and the mixture warmed on the water bath for a few min- 

 utes. When cool, the large excess of aniline was removed by dilute 

 sulphuric acid, and, after thorough washing, the dark-colored residue 

 was purified by dissolving it in aniline, and then adding a small quan- 

 tity of alcohol ; in this way well formed dark brown crystals were 

 obtained, melting at 287°-290°, and therefore probably the dichlor- 

 dianilidoquinone, the melting point of which is given as 285°-290°. 

 This substance was first prepared and studied by O. Hesse,* later by 

 Knapp and Schultz.t To confirm this inference the crystals were dried 

 at 100° and the chlorine determined. 



0.1480 gram of the substance gave by the method of Carius 0.1174 

 gram of argentic chloride. 



Chlorine 



The reaction therefore took an unexpected course, since the anilido 

 groups replaced the two phenoxy radicals instead of the two atoms of 

 chlorine. 



Action of Sodium Malonic Ester on Dichlordiphenoxyquinone. 



It has been shown in the preceding section that aniline removes the 

 phenoxy groups instead of the atoms of chlorine from dichlordiphenoxy- 

 quinone. We therefore next turned our attention to the action of 

 sodium malonic ester upon it to see whether this reagent behaved in 

 the same way. In order to study this reaction 1 gram of dichlordi- 

 phenoxyquinone suspended in 10 c.c. of absolute alcohol was treated 



* Ann. Chem., CXIV. 306. t Ibid., CCX. 187. 



