426 PROCEEDINGS OF THE AMERICAN ACADEMY. 



with a little more than two equivalents of sodium malonic ester, which 

 was made by treating 0.15 gram of metallic sodium with about 10 c.c. 

 of absolute alcohol, and then adding 2 grams of malonic ester. On 

 adding tlie sodium malonic ester, the solution turned very dark blue, 

 and un standing a dark blue precipitate separated, which was filtered 

 off and washed with alcohol, in which it is only slightly soluble. The 

 precipitate dissolved readily in water with a beautiful blue color, and 

 on the addition of an acid a slightly yellow crystalline product sepa- 

 rated, which was purified by recrystallization from boiling dilute 

 ali-oiiol until it gave the constant melting point 132°. After drying 

 at 100°, it gave the following results on analysis: — 



I. 0.2180 gram of the substance gave on combustion 0.3880 gram of 

 carbonic dioxide and 0.0994 gram of water. 

 II. 0.1654 gram of the substance gave 0.0964 gram of argentic 

 chloride. 



These results prove that ihe substance is dichlorquinonedimalonic 

 ester. Four grams of the dichlordiphenoxyquinone gave a yield of 

 about 1.5 grams of the malonic ester compound, that is, 27 per cent of 

 the theoretical yield. 



It is evident that this body must be formed through the replace- 

 ment of the two phenoxy groups by two malonic ester radicals, and 

 in fact it was not hard to detect the phenol, which formed the second- 

 ary product of the reaction. For this purpose the alcoholic filtrate 

 from the sodium salt of the malonic ester derivative, after evaporation 

 nearly to dryness, was diluted with water, and treated with a dilute 

 acid, when the smell of phenol was very evident, and bromine water 

 gave a voluminous white precipitate. This easy replacement of the 

 phenoxy groups by the malonic ester radicals, even although the for- 

 mer are attached to a benzol ring, suggests other work in the same 

 line, which will be undertaken in this Laboratory, 



This dichlorquinonedimalonic ester crystallizes from dilute alcohol 

 in long slender radiating needles of a yellow color, which melt at 

 132°, and are insoluble in cold or boiling water, soluble in cold or 

 warm alcohol. It is not affected by weak oxidizing agents, but hydri- 

 odic acid reduces it to a white crystalline substance, which melts at 



