CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 



HARVARD COLLEGE. 



ON THE OXIDE OF DICHLORMETHOXYQUINONEDIBEN- 



ZOYLMETHYLACETAL* 



By C. Loring Jackson and H. A. Torrey. 



Presented May 12, 1897. 



A PAPER on the acetals derived from substituted quinones published 

 by H. S. Griudley and one of us in 1895, contained a description f of a 

 substance made by the action of sulphuric acid on the dichlordimethoxy- 

 quinonedibenzoyldimethylacetal, which had the formula 



CcCl,(OCH3)o(OCOCeH5)A 



and which was called then the oxide of dichlordimethoxyhydroquinonedi- 

 benzoate ; a name which the better knowledge of its constitution obtained 

 from the work described in this paper makes it necessary for us to change 

 to oxide of dichlormethoxyquinonedibenzoylmethylacetal. 



As it seemed probable that the atom of oxygen in this substance was 

 attached to two of the carbon atoms of the benzol ring, we decided to 

 continue the study of it, and we describe the results of our work in this 

 paper. In the preceding paper nothing had been done with this body 

 beyond establishing its composition and that of the corresponding ethyl 

 compound, and the preparation and partial study of a reduction product 

 obtained from the ethyl oxide by the action of hydriodic acid. 



In taking up again the study of the oxide the first point to be deter- 

 mined was whether the atom of oxygen is attached to one atom of car- 

 bon or to two. In the former case the substance must be either a ketone 

 or a phenol. In writing the formula of this substance on the supposi- 

 tion that it is a ketone, it is necessary to assume such improbable in- 

 tramolecular transformations that we felt inclined to reject the ketone 

 formula on this ground alone ; and this theoretical deduction was con- 



* Tlie work described in this paper formed part of a thesis presented to the 

 Faculty of Arts and Sciences of Harvard University for the Degree of Doctor of 

 Pliilosophy, by H. A. Torrey. 



t These Proceedings, XXX. 440. 



