434 PROCEEDINGS OF THE AMERICAN ACADEMY. 



sary to boil it with a strong solution of sodic hydrate in order to 

 saponify it to chloranilic acid. The sodium salt of the diethylhemia- 

 cetal is white and crystalline, readily soluble in water^ slightly soluble 

 in alcohol, and insoluble in ether. The dried salt is slowly decom- 

 posed on standing in a closed bottle for several weeks, alcohol is given 

 off, and a solid product left, which contains some sodic chloranilate 

 and another body, or more than one, which we have not yet identified. 

 The silver salt is insoluble, and has a slight brownish yellow color. 

 It is blackened by light alcohol being set free. On warming with 

 water a red substance is formed, probably chloranilic acid. Insoluble 

 salts were also obtained with solutions containing barium, calcium, 

 lead, or zinc, but they were not studied. The details of the prepara- 

 tion of the sodium and silver salts will be found under the preparation 

 of dichlordiethoxyquiuone tetraethylacetal later in this paper. 



Dichlordim ethoxyqidnone Diethylhemiacetal, 



CeCl2(OCH3)2(OH)2(OC2H5)2. 



This substance was made by treating 0.9 gram of dichlordimethoxy- 

 quinone with an alcoholic solution of sodic ethylate made from 0.2 

 gram of metallic sodium and absolute alcohol. After warming the 

 mixture for a few minutes, all the red dichlordimethoxyquinone disap- 

 peared, and a crystalline sodium salt was deposited. The liquid was 

 then cooled, the precipitate filtered out, washed with a little alcohol, and 

 dissolved in water, in which it is completely and easily soluble. The 

 aqueous liquid after filtration was treated with dilute sulphuric acid, 

 which threw down a white bulky precipitate of the free hemiacetal, 

 and this, after thorough washing with water, alcohol, and ether, was 

 dried over sulphuric acid and paraffine, and analyzed with the follow- 

 ing result : — 



0.1892 gram of the substance gave by the method of Carius 0.1 G27 

 gram of argentic chloride. 



Calculated for 

 CeCl, 0CH3)2(0H)2(0C2H6)2. Found. 



Chlorine 21.58 21.26 



The dichlordimethoxyquinone diethylhemiacetal, like those hemia- 

 cetals which have been described already, is an amorphous white solid, 

 essentially insoluble in all the common solvents. It is decomposed at 

 temperatures between 140° and 160°, forming a red substance, prob- 

 ably dichlordimethoxyquinone, and it is easily saponified by dilute 

 acids. 



