OP ARTS A^D SCIENCES. 



301 



The compound is easily soluble in benzine and chloroform, less so 

 in alcohol, acetic acid, and ether. It dissolves in dilute alkalies, mild 

 or caustic, forming deep bluish violet solutions, which soon change to 

 brown. Sodic nitrite reacts on an alcoholic solution in the cold, form- 

 ing a yellow substance which crystallizes in prisms, melts at 184°, and 

 contains both chlorine and nitrogen. Fuming nitric acid converts the 

 quinone into a very unstable yellow substance. An alcoholic solution 

 is colored deep blood-red by addition of ferric chloride. One of the 

 noteworthy properties is the ease with which the quinone forms addi- 

 tion products, and these are treated specially further on. A great 

 many experiments were made in order to prove that the two aceto- 

 acetic ether groups are in the para position, but without success. This 

 is, however, extremely probable, since in all cases yet known where 

 two chlorine atoms in chloranil have been replaced the substitution 

 takes place in para position (compare also Stieglitz, where two ma- 

 lonic ether groups are introduced in the para position*). 



p-Dichlorhydroquinonediacetoacetic Ether ^ C6C1o(OH)2(CgH903)2. 



The above quinone is reduced to the hydroquinone in exactly the 

 same way as described under trichlorhydroquinoneacetoacetic ether. 

 The solid obtained by adding water to the alcoholic solution is purified 

 by crystallization from benzine, from which solvent it separates out in 

 colorless transparent rhombohedra, melting at 154°. 



0.2114 gram substance dried at 130° gave 0.3816 gram CO2 and 

 0.0881 gram H^O. 



In its behavior towards ferric chloride, alkalies, and solvents, the 

 hydroquinone is quite similar to trichlorhydroquinoneacetoacetic ether. 

 The substance treated with dehydrating agents loses two molecules of 

 water with ease, going over into a benzodifurfuran derivative. 



* American Chem. Journal, XIII. 38. 



