JACKSON AND GRINDLEY. — ACETALS PROM QUINONES. 451 



a non-crystalliue body insoluble in water, but soluble in sodic hydrate 

 with a fine purple color. We have not had time as yet to study this 

 substance more carefully. 



When the yellow dimethoxydiphenoxyquinone was mixed with a 

 solution of sodic methylate in methyl alcohol, and the mixture stirred 

 vigorously, the yellow solid disappeared, and a white crystalline 

 sodium salt was precipitated. This precipitate dissolved in water 

 without residue, and from the solution the addition of a dilute acid 

 threw down a white amorphous solid, which decomposed almost 

 immediately into a yellow substance probably dimethoxydiphenoxy- 

 quinone. These observations show that in this case a hemiacetal was 

 formed, but a much less stable one than that obtained from the 

 quinones containing chlorine. It seems, therefore, that the stability 

 of the hemiacetals depends on the number and strength of the negative 

 radicals attached to the quinone ring. 



Action of Sodic Phenylate on Bromanil. 



In order to study this action 2 grams of bromanil, prepared accord- 

 inor to Stenhouse,* were treated with an alcoholic solutionf of sodic 

 phenylate made by acting on 0.3 gram of sodium with absolute alcohol 

 and then adding 3 grams of phenol. The bromanil began to turn 

 red as soon as the phenylate was added, but it was necessary to warm 

 the mixture in order to make the reaction complete. After this the 

 solution was filtered, and the solid remaining on the filter, after 

 thorough washing with water and alcohol, was purified by crystalliza- 

 tion from benzol until it showed the constant melting point 2G6°- 

 267°, when it was dried at 100° and analyzed with the following 

 result : — 



0.1677 gram of the substance gave, according to the method of 

 Carius, 0.1393 gram of argentic bromide. 



Calculated for 

 C6B^2(0CgHg^202 Found. 



Bromine 35.56 35.36 



The substance is, therefore, dibromdiphenoxyquinone, and it is to 

 be observed that bromanil behaves differently from chloranil with this 



* Ann. Chem., Suppl. VIII. 13. 



t This experiment was tried early in our work, before we had found that an 

 aqueous solution of the sodic phenylate acted better on chloranil than the 

 same reagent dissolved in alcohol. If we were to repeat this preparation, 

 therefore, we should use a solution in water instead of in alcohol. 



