296 PROCEEDINGS OF THE AMERICAN ACADEMY 



off, and the last traces of it removed by prolonged heating in an open 

 dish on a water bath. A dark orange-colored oil is left, which is a 

 mixture of acetoacetic ether, and the mono- and the di-substituted 

 acetoacetic ether derivatives of chloranil. On adding a small amount 

 of absolute alcohol, and stirring, the oil gradually solidifies to a crys- 

 talline mass. Recrystallized from alcohol, large orange rhombohedra 

 of trichlorquinoneacetoacetic ether are obtained, as well as yellow 

 rhombic crystals of dichlorquinonediacetoacetic ether, which two sub- 

 stances can readily be separated mechanically from one another; the 

 latter is also somewhat less soluble in alcohol. 



The red mono-substitution product was recrystallized from alcohol 

 until it showed the constant melting point 94°, and then dried at 70° 

 to 75° and analyzed. 



0.3014 gram substance gave 0.4737 gram COg and 0.0738 gram HgO. 

 0.2524 " " " 0.3158 " AgCl (Carius). 



Trichlorquinoneacetoacetic ether is easily soluble in benzine, warm 

 alcohol, and chloroform, moderately so in acetic acid, and difficultly 

 soluble in ether. It dissolves in dilute alkalies and ammonia with blue 

 color, changing quickly to orange-yellow on standing. An alcoholic 

 solution of the substance gives a blood-red coloration with ferric chlo- 

 ride. With aniline it forms a colorless addition product melting at 

 146°, whereas fuming nitric acid changes it into a yellow very unsta- 

 ble substance. Reducing agents readily convert it into the corre- 

 sponding hydroquinone. 



Trichlorhydroquinoneacetoacetic Ether, C6Cl3(OH)2(CeH903). 



The reduction of the quinone can be effected quantitatively by dis- 

 solving it in about 6 parts of alcohol, and adding alternately zinc dust 

 and dilute sulphuric acid in small quantity until the solution becomes 

 colorless. On adding water the hydroquinone separates out as an oil, 

 which soon solidifies. Recrystallized from benzine, it is obtained in 

 colorless rhombohedra, melting at 132°. 



0.2204 gram substance dried at 105° gave 0.3444 gram COg and 

 0.0707 gram H2O. 



