JACKSON AND TORRET. — AN ORGANIC OXIDE. 151 



Action of Sodic Methylate on the Methyl Oxide 

 C6Cl20CH30(OCOC6H5)20CH3. 



One gram of the oxide was added to a solution of sodic methylate made 

 by the action of 0.2 gram of metallic sodium on 10 c. c. of methyl al- 

 cohol. After heatinoj the mixture for a short time on the water bath the 

 liquid became slightly yellow, and the oxide went into solution, but soon 

 after a white substance was deposited, the quantity of which increased as 

 the liquid cooled; at the same time the odor of benzoic methylester was 

 observed. The product of the reaction was allowed to stand at ordinary 

 temperatures for half an hour, after which the white precipitate was 

 collected on a filter, and washed at first with methyl alcohol, in which it 

 is only slightly soluble, and finally with ether. The washed precipitate 

 was then dissolved in water, and the solution, after it had been filtered, 

 acidified with dilute hydrochloric acid. The white flocculent precipitate 

 formed by the acid was washed thoroughly with water, alcohol, and 

 ether; and next redissolved in sodic hydrate, filtered, and reprecipitated 

 with dilute hydrochloric acid. These solutions and reprecipitations were 

 repeated several times until the precipitate was perfectly white. 



The amorphous white substance thus obtained was very similar in 

 appearance to a hemiacetal. It was dried and analyzed with the follow- 

 ing result : — 



0.1368 gram of the substance gave by the method of Carius 0.1300 gram 

 of argentic chloride. 



Calculated for C6Cl,(0CH3),(0H)o(0CH3)2. Found. 



Chlorine 23.59' ' 23.49 



This analysis indicates that the substance is the dichlordimethoxyqui- 

 nonedimethylhemiacetal, and this view of its composition is confirmed by 

 the following experiment. A small quantity of the substance was heated 

 with dilute hydrochloric acid, when a red crystalline body was obtained 

 melting in the crude state at 140°, after recrystallization at 141°. This 

 must therefore have been the dichlordimethoxyquinone whose melting 

 point is 141°-142°. 



The hemiacetal could be formed from the oxide by the following 

 reactions : — 



CeCI.OCH30(OCOC,.H-),OCH3 + NaOCHs = 

 CsCl2(OCH3)„ONa(OCOC,H5)oOCH3 = 

 CgH^COONa + CsHgCOOCHg + 6^01.(00 FlglA. 



An odor of benzoic methylester was observed, as already stated. 

 C6Cl2(OCH3).A + 2NaOCH3 = C,.Cl2(OCH3)o(ONa),fOCH3)o. 



