JACKSON AND GRINDLEY. — ACETALS FROM QUINONES. 411 



Sodic inetliylate acted on the dichlordipheuoxyquiuoue like the two 

 reageuts ali'eady mentioued ; that is, the two pheuoxy groups were 

 replaced by two methoxy groups ; but this action was followed by 

 another and more interesting one, which formed a crystalline salt, 

 appearing as a precipitate, if the amount of methylalcohol used as the 

 solvent was small. Upon the addition of an acid to this salt a white 

 substance was set free having the followiug formula: 



C,C\,(OCB.,).fi.,(CU,OH),. 



The sodium salt was also analyzed, and proved to have the formula 



C6Cl2(OCIl3)oO,(CH30Na)2(CH30H)2. 



The two molecules of methyl alcohol appearing in this last formula 

 are evidently only alcohol of crystallization, as they could be easily 

 driven off by heat. The corresponding ethyl compound, 



and the methylethyl compound, 



C,Clo(OCH3)202(aH50H)2,' 



were also obtained, and resembled the methyl compound most closely 

 in properties. In considering the way in which the two molecules of 

 methyl alcohol (or sodic methylate) are attached to the molecule of 

 CgCL,(OCH3)202, only two formulas seemed to us sufficiently probable 

 to merit discussion. In the first of these (I.) the double bonds of the 

 benzol ring are broken, and the radicals NaO and CHg added directly 

 to the ring after the manner of the bromine and chlorine addition 

 ■compounds discovered by Nef.* In the second (II.) the NaO and CHg 

 have been added to the two carbonyl groups of the quinone, transform- 

 ing it into a substance closely related to the acetals. 



I. II. 



O CH3-O 0-Na 



II \ / 



c c 



CH,-0\p/ \p/Cl / \ 



Na-0/'" ^\CH3 CH3O-C C-Cl 



CH3\ 



/0-Na 



ci ; c ^ / c c 6-hk ^^-\ /-OCH3 



C 



II 



o 



c 



/ \ 

 Na-0 OCH3 



* Am. Chem. Journ., XII. 483; XIII. 422. 



