JACKSON AND GRINDLEY. — ACETALS FROM QUINONES. 447 



This body can also be formed by the action of four equivaleuts of 

 potassic pheuylate in aqueous solution on chloraml, or by the at-tion 

 of sodic phenylate on the dichlordiphenoxyquinone suspended in 

 benzol. In this latter case the sodic phenylate was prepared by 

 dissolving phenol in a rather large volume of benzol, and then adding 

 the required quantity of sodium, which disa|)peared completely alter 

 warminc the solution on the steam bath for some time. Neither of 

 these methods gives so good a result as the one described at the be- 

 ginning of this section. On the other hand, the tetraphcnoxyquinone 

 is not formed when the dichlordiphenoxyquinone is treated witli sodic 

 phenylate, which has been made by the action of metallic sodium on 

 absolute alcohol mixed with phenol, as in this case the principal pro- 

 duct is diethoxydiphenoxyquinone. 



Properties of Tetraphenoxyquinoiie. — It crystallizes from benzol 

 in red prisms which, when well developed, have blunt ends formed by 

 a number of planes or by a single plane at an oblique angle. When 

 smaller they appear as long somewhat shuttle-shaped prisms, radiating 

 from a common centre, but not forming circular groups. It melts at 

 229°-230°, and is soluble in hot chloroform, boiling acetic anhydride, 

 or boiling benzol ; slightly soluble in carbonic disulphide, or boiling 

 glacial acetic acid ; very sparingly in warm acetone ; insoluble in 

 water, alcohol, ether, or ligroine. The best solvent for it is boiling 

 benzol. 



The tetraphenoxy qui none is not easily attacked by reducing agents ; 

 sulphurous acid at ordinary temperatures, or in a sealed tube at 100°, 

 has no action on it ; hydriodic acid, or a mixture of stannous chloride 

 and hydrochloric acid, reduces it, but the action is very slow ; on the 

 other hand, it is easily reduced by glacial acetic acid and zinc dust. 



Saponification of Tetraphenoxyquinone. 



Toward acid saponifying agents the tetraphenoxyquinone shows a 

 remarkable stability. Sulphuric acid of specific gravity 1.44 has no 

 effect whatever, even after long continued boiling, but hot strong 

 sulphuric acid of specific gravity 1.83 dissolves it, giving a solution 

 from which nothing is precipitated on adding water. This may be 

 due to the formation of a sulphonic acid, but we have not as yet 

 studied the reaction carefully. 



A better result was obtained by boiling the tetraphenoxyquinone 

 with a solution of sodic hydrate (one part in four) for ;ibout two hours, 

 as it was then completely dissolved, giving a dark purple color to the 

 solution, which on cooling deposited small black crystals of a sodium 



