JACKSON AND GRINDLEY. — ACETALS FROM QUINONES. 453 



188°, at the same time changing to a red substance, probably dibrom- 

 dimethoxyquinone. This change can also be produced by treatment 

 with dilute sulphuric acid, or dilute hydrochloric acid. From this 

 description of the preparation and properties of this hemiacetal it is 

 evident that the action of sodic methylate on dibromdiphenoxyquinone 

 is similar in every respect to the action of this reagent on the corre- 

 sponding compound containing chlorine. 



Action of Potassic Phenylctte on Trichlorqidnone. 



By treating 5 grams of trichlorquinone suspended in water with 

 two equivalents of potassic phenylate, made from 2.7 grams of potassic 

 hydrate and 8 grams of phenol, a red serai-liquid substance was 

 formed. After the mixture had been heated on the steam bath for 

 twenty minutes in order to complete the reaction, the supernatant 

 liquid was poured off, and the pasty residue washed with water by 

 decantation, and then warmed with alcohol, which converted it into 

 a crystalline solid. These crystals were then separated by filtration, 

 washed thoroughly with cold alcohol, and recrystallized from alcohol 

 containing a small amount of benzol until they showed the constant 

 melting point 169° -170°, when they were dried at 100°, and analyzed 

 with the following results : — • 



I. 0.1888 gram of the substance gave by the method of Carius 0.0818 



gram of argentic chloride. 

 II. 0.1913 gram gave 0.0832 gram of argentic chloride. 



Calculated for Found. 



C6HC1(0C6H3)203. I n. 



Chlorine 10.87 10.71 10.75 



Properties of Monochlordiphenoxyqidnone. — It crystallizes from 

 alcohol in long, slender, pointed oval blades arranged in irregular 

 groups, — a very charactei'istic habit of crystallization. It has an 

 orange color, with a slight brownish tinge, and melts at 169°-170°. 

 It is easily soluble in benzol or chloroform ; difficultly soluble in alco- 

 hol ; slightly soluble in carbonic disulphide ; insoluble in water, ether, 

 or ligroine. It is easily reduced to a colorless hydroquinone by glacial 

 acetic acid and zinc dust. 



To see whether it would form a hemiacetal 0.5 gram of the mono- 

 chlordiphenoxyquinone was treated with the sodic methylate made 

 by acting on 0.3 gram of metallic sodium with a few cubic centimeters 

 of methyl alcohol. The quinone dissolved in the cold, but, even when 

 allowed to stand for some time and stirred vigorously, no precipitate 



