152 PROCEEDINGS OP THE AMERICAN ACADEMY. 



Action of Sodic Meihylate on the Ethyl Oxide 

 C,CL(OC,H,)0(OCOC„H,),OC,H,. 

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

 made by the action of 0.2 gram of sodium on 12 c. c. of methyl alcohol. 

 The oxide went into solution at once, but after the solution had been 

 heated on the steam bath for a short time a white precipitate was thrown 

 down, the amount of which was increased by the addition of ether. 

 After purification by alternate precipitation by hydrochloric acid, and 

 solution in sodic hydrate, as described in the preceding section, the 

 substance was dried in a desiccator, and analyzed with the following 

 result : — 



0.1527 gram of the free hemiacetal gave by the method of Carius 0.1450 

 gram of argentic chloride. 



Calculated for C6Clo(OCH3)2(OII)2(OCH3)2. Found. 



Chlorine 23.59" " 23.58 



As the mixed ethyl methylhemiacetal, which would be expected here, 

 contains 21.58 per cent of chlorine, there can be no doubt that the pro- 

 duct was the dimethylhemiacetal ; and this view was confirmed by the 

 following experiment. A small quantity of the substance was heated 

 with dilute hydrochloric acid, when a red solid was formed which melted 

 at 140°, and therefore was the dichlordimethoxyquinone. From these 

 observations it follows that the behavior of the ethyl oxide with sodic 

 methylate is the same as that of the methyl oxide, except that, in ad- 

 dition to the formation of the hemiacetal, the ethoxy groups have been 

 I'eplaced by methoxy groups. 



After the work just described had shown that ethoxy groups in the 

 ethyl oxide could be replaced by methoxy groups under the influence of 

 sodic methylate, the following experiment was tried to see whether a 

 similar change could be produced with the dichlordiethoxyquinone : 0.7 

 gram of this substance were treated with a solution of the sodic methylate 

 made from 0.2 gram of sodium and 5 c. c. of methyl alcohol ; the hemi- 

 acetal formed was decomposed with dilute hydrochloric acid, and the red 

 quinone obtained recrystallized from alcohol, and then from benzol, when 

 it melted at 139°, showing that it was dichlordimethoxyquinone, and 

 therefore that the methoxy groups had replaced the ethoxy gi-oups in 

 this case also, as was to be expected. 



We next tried an experiment to see whether the reverse change could 

 be brought about. One gram of the methyl oxide, 



c,ci.,ocii,o(ococ,;ig20CH3, 



