JACKSON AND KOCH. — DERIVATIVES OF ORTHOBENZOQUINONE. 211 



cide between these formulas, as the ether should be split into pyrocate- 

 chine and a trioxybenzol, while the diphenyl product would be reduced 

 without splitting apart the two benzol rings. Upon treating the black 

 alteration product with sodium amalgam and water in an atmosphere of 

 carbonic dioxide for several days, an uninviting black solid was obtained 

 on acidification, which was soaked in water, and this water as well as the 

 acidified filtrate from the reduction extracted with ether, but not a trace 

 of pyrocatechine was obtained. As the bromether, which we have ob- 

 tained in another part of our work, gives a large quantity of pyrocate- 

 chine by this treatment, we infer that the black alteration product is a 

 diphenyl derivative. 



Action of Benzoylchloride on the Black Alteration Product. 



Half a gram of this substance was dissolved in 10 c.c. of a solution of 

 potassic hydrate (1:5), and to the warm solution benzoyl chloride was 

 added drop by drop, until the product of the reaction rose to the surface 

 as an oily mass, leaving the liquid clear. This was then treated with 

 sodic hydrate, in which it did not dissolve, and thoroughly washed with 

 water. The tarry mass thus obtained was dissolved in chloroform, the 

 solution filtered, and the filtrate mixed with an excess of alcohol, which 

 preciptated out the substance. After drying in vacuo it was analyzed, 

 with the following result: — 



0.2210 gram of the substance gave on combustion 0.5933 gram of carbonic 

 dioxide and 0.0744 * gram of water. 



Found. 



Carbon 70.91 72.79 73.21 



Hydrogen 3.64 3.68 3.74 



The substance is therefore a tribenzoyl compound, and the original black 

 body must have contained three hydroxy! groups. This benzoxyorthoquino- 

 orthodibenzoxydiphenyl, C 6 H 2 (OCOC 6 H 5 )0 2 C 6 H 3 (OCOC 6 H 5 ) 2 , f forms a 

 light yellow amorphous powder without a definite melting point. It is 

 easily soluble in chloroform ; insoluble in alcohol or water. Alkalies do 

 not dissolve it. 



The fact that only three benzoyl groups are taken up by the black 

 alteration product indicates that two of its five atoms of oxygen do not 



* A little water was lost in this analj-sis. 



t The distribution of the benzoxy groups in this substance has not been 

 determined. 



