JACKSON AND GRINDLEY. — ACETALS FROM QUINONES. 4l5 



ative. Zincke and Neumann,* by the action of alcohol on nitro-y8- 

 naphthoquinone, obtained a substance the formula of which was made 

 out as follows : — 



O 



II /OH 



/ , ^wi^ng 



/N( 

 \H 



C6H4 ^ I -^Q_^ 



\ • / 



C-C 

 / \ 

 H OCH 



Still later, Zincke and Schaum f have made similar compounds from 

 the isomeric heptachlorketotetrahydrobenzols by the action of sodic 

 methylate. Although Zincke's work shows that ring ketones, ortho- 

 diketones, and orthoquinones are capable of forming such hemiacetals, 

 so far as we can find our compound is the first of this class to be made 

 from a paraquinone, and the compound of Zincke's which approaches 

 most nearly to it, the orthoquiuone derivative, differs from it strikingly, 

 for, whereas in our compound both carbonyls are converted into hemi- 

 acetal groups, in Zincke and Neumann's only one of the carbonyl 

 groups is thus affected, and at the same time a molecule of sodic 

 methylate is added to the ring by the breaking of a double bond. It 

 should be mentioned here that J. U. Nef $ has assumed the formation 

 of addition products of water or hydrochloric acid with the carbonyls 

 of quinone in explaining the formation of hydroquinone by the action 

 of water,§ or substituted hydroquinones by the action of hydrochloric 

 acid on quinone ; II but he supposes that these intermediate products 

 break up immediately, and none of them have been isolated. 



The discovery of the hemiacetals of the quinones has suggested to 

 us a possible explanation of the constitution of quinhydrone and the 

 bodies related to it. The most important of these substances are 

 quinhydrone, formed from one molecule of quinone and one of hydro- 

 quinone ; resorcinequinone, from one molecule of quinone and one of 

 resorcine ; phenoquinone, from one molecule of quinone and two of 

 phenol ; and quinhydronedimethylether, from one molecule of quinone 

 and two of the monomethylether of hydroquinone. The state of our 



* Ann. Cheni., CCLXXVIII. 173. 

 t Ber. d. cli. G., XXVII. 5-37. 



t Am. Cliem. -Journ., XIII. 427; Ann. Chem., CCLXX. 323; Clark, Am. 

 Chem. Journ., XIV. 55.3. 



§ Hesse, Ann. Chem., CCXX. 367; Ciamician, Gazz. Chim., XVI. 111. 

 II Levy, Schultz, Ann. Chem., CCX. 133; Sarauw, Ibid., CCIX. 93. 



