JACKSON AND GRINDLEY. — ACETALS FROM QUINONES. 418 



To obtain material for this work, which would be possessed of the 

 requisite stability, we replaced the sodium in the salt of our substance 

 with the benzoyl radical forming a compound which must have one of 

 the following formulas, according as one or the other hypothesis about 

 these substances is adojjted. 



I. II. 



O C2H5-O O-COCsHs 



II \ / 



c c 



aH,-0\^/ \r./Ci / \ 



J ..r. f^ .^ ^^ (.^pj^ C^H.-O-C C-Cl 



CsH.CO-O/ 

 C,H,.\ 



ci/-w-<olS&''^ ci-c^ ^c-o-cw. 

 c c 



II / \ 



O CeHjCO-O O-C.Hg 



In Formula I. the carbonyl groups are unaffected, and the body 

 should therefore retain the properties of a diketoue. In Formula II., 

 on the other hand, the carbonyl groups having been transformed 

 into acetal groups, the body should have lost its diketone nature. 

 Accordingly, a substance constituted like Formula I. should be con- 

 verted by reducing agents into a substance containing secondary 

 hydroxyl groups, and by the chloride of hydroxylamine into a mono 

 or dioxime. Upon treating our substance with zinc dust and glacial 

 acetic acid, (which we have found the most efficient agent for con- 

 verting quinones into hydroquinones,) it remained entirely unaltered, 

 and the same result was obtained when we tried to act on it with 

 chloride of hydroxylamine. The substance therefore shows neither 

 of these characteristic reactions of the diketones and must be consti- 

 tuted according to Formula II. To meet the not overstrong objec- 

 tion that the diketone properties of the substance might have been 

 weakened or destroyed by the presence of radicals attached to the 

 ring, we treated dichlordiethoxyquinone with the reducing mixture, 

 and also with chloride of hydroxylamine, and in both cases obtained a 

 satisfactory quinone reaction. We tried also to determine the consti- 

 tution of our substance in another way. This consisted in making the 

 dichlordiethoxyquinone tetraethylacetal C6C12(OCoH5).t(OC.2H5)4 by re- 

 placing the sodium in the sodium salt C6Cl2(OC.2H5)2(ONa)2(OCoH5)2 

 by ethyl, and then treating this dissolved in chloroform with bromine 

 in the hope of making an addition product similar to those of Nef, The 



