JACKSON AND GRINDLEY. — ACETALS FROM QUINONES. 423 



Experimental Part. 

 Action of Potassic Phenylate on Chloranil. 



In order to study this action, 25 grams of chloranil suspended in 

 50 c. c. of water were treated with au aqueous solution of pota-ssic 

 phenylate, made from 12 grams of potassic hydrate and 25 giams of 

 phenol, which gave the proportion of two molecules of potassic phe- 

 nylate to one of chloranil. To obtain a good result in this process it 

 was necessary that the chloranil should not be in too large crystals ; 

 if, therefore, the specimen used was well crystallized, it was reduced 

 to the hydroquinone with sulphurous acid, and then oxidized with 

 nitric acid, which left it in a finely divided form easily attacked by 

 the solution of potassic phenylate. The potassic phenylate was added 

 in small portions at a time, and the first few drops imparted to the 

 liquid a chrome-green color, which gradually changed to blue-black 

 as more of the solution was added, until at last the whole became very 

 dark blue or nearly black. In order to complete the reaction the 

 mixture was heated on the steam bath for thirty minutes, which 

 changed the color from black to red. In the cold there were no siirns 

 of the formation of this red substance, but it began to appear as soon 

 as the mixture was warmed. The solution was filtered, and the dark 

 red solid remaining on the filter, after washing thoroughly with water 

 and alcohol, was purified by crystallization from hot benzol until it 

 showed the constant melting point of 243°. 



The analysis of the substance dried at 100° gave the following 

 results : — 



I. 0.2138 gram of the substance gave on combustion 0.4692 gram of 

 carbonic dioxide and 0.0637 gram of water. 

 II. 0.1510 gram of the substance gave, according to the method of 

 Carius, 0.1206 gram of argentic chloride- 

 Found. 



II. 



19.75 



From these results it is evident that the substance is dichlordiphe- 

 •noxyquinone. The yield is very good, 25 grams of chloranil giving as 

 a rule 26 to 30 grams of the new substance, that is, about 80 per cent 

 of the theoretical yield. 



