428 PROCEEDINGS OF THE AMERICAN ACADEMY. 



0.2010 gram of the suUstauce gave on combustion 0.4122 gram of 

 carbonic dioxide and 0.1242 irram of water. 



It gave no teat for chlorine. These results prove that the substance 

 is diethoxyquinonedimalonic ester, and it is certainly strange that this 

 substance sliould have been formed from the corresponding dichlor 

 compound by the action of sodic carbonate and alcohol, in view of 

 the fact that these two atoms of chlorine in other cases have proved 

 hard to replace. The substance crystallizes in beautiful yellowish 

 white needles melting at 115°, which are insoluble in water, readily 

 soluble in alcohol or ether. 



Action of Sodic Methylate on Dichlordiphenoxyquinone. — Dlchlordime- 

 thoxyquinone DlmethyJhemiacetal, C6Clo(0 0113)0(011)0(00113)2. 



In order to see whether the phenoxy groups in dichlordiphenoxy- 

 quinone would be removed by sodic methylate, as they were when it 

 was treated with sodium malonic ester or aniline, 10 grams of the 

 dichlordiphenoxyquinone were mixed with a methyl alcohol solution 

 of a little less than four equivalents of sodic methylate, made by treat- 

 ing 2.5 grams of metallic sodium with 60 c.c. of methyl alcohol. The 

 solution was warmed gently on the water bath, and stirred constantly ; 

 soon a white crystalline substance began to separate, and the red color 

 of the dichlordiphenoxyquinone disappeared entirely. The solution 

 was filtered, the residue washed with a little alcohol, dissolved in 

 water, filtered again, and then treated with dilute sulphuric acid in 

 excess, which set free a white insoluble compound. The proper- 

 ties of this substance indicated at once that the reaction bad not con- 

 sisted in a simple replacement of the phenoxy by methoxy groups, 

 as in that case the product must have been the dichlordimethoxy- 

 quinone discovered by Kehrmann,* which is red, melts at 141°-142°, 

 and is not insoluble in the common solvents. To prepare our new 

 body for analysis it was filtered off, washed with water, alcohol, and 

 then with water again ; after which it was dissolved in dilute sodic 

 hydrate, filtered, precipitated with dilute sulphuric acid, and washed 

 thoroughly as described above. This treatment was repeated two or 

 three times, until the substance was perfectly white and did not change 



* Journ. Prakt. Chem., [2.], XL. 370. 



