148 PROCEEDINGS OF THE AMERICAN ACADEMY. 



that the ethoxy groups could be replaced by methoxy groups, or the re- 

 verse, when one of our compounds was treated with the sodic alcoholate 

 containing the radical, which was not already attached to its quiuone ring.* 

 The acetyl acetals corresponding to the benzoyl acetals have also been 

 made by us, and have the following melting points : — 



C6Clo(OCH;3)„(OCH3)2(OCOCH3)o, melting point 177° to 178°; 

 C6CL(OC2H5)o(OCoH5)2(OCOCH3)2, melting point 120° to 121°. 



We also describe some experiments on the action of sodic alcoholates 

 on quinone itself and on chlorauil, which led to substances probably simi- 

 lar to the colored compounds obtained from nitro aromatic bodies by the 

 action of sodic alcoholates by Lobry de Bruyn,t Victor Meyer,t and 

 Ittner and one of us.§ These experiments were abandoned after some 

 progress had been made on account of the work of Astre || in the same 

 field, and are described here only because they cannot be brought into har- 

 mony with the theory advanced by Astre to account for these substances. 

 The discussion of this question will be found in the experimental part. 



We also observed that an alkaline solution of sodic chloranilate was 

 converted into iodoform by treatment with iodine. 



Experimental Part. 



Preparation of the Oxide of Dicldormethoxyquinonedibenzoylmethylacetal, 



C6CLOCH30(C02C6H5)oOCH3. 



This preparation was carried on essentially in the manner described 

 by Grindley and one of us in a previous paper,1[ but we think it best to 

 describe the process again here, as in that paper it is not given continu- 

 ously, but scattered through different paragraphs, and also because we 

 have introduced a few improvements in the details. 



To convert chloranil into dichlordiphenoxyquinone fifty grams of chlor- 

 anil, previously converted to a fine powder by I'eduction to tetrachlor- 

 hydroquinone by sulphurous acid followed by oxidation with nitric 

 acid,** were treated with a strong aqueous solution of potassic phenylate 



* Compare Gattermann and Kitsclike, Ber. d. cliern. Ges., XXIII. 1738 (1890). 

 t Rec. Trav. Chim. Pays Bas, XIV. 89. 

 I Ber. d. cheni. Ges., XXVII. 3153. 

 § Am. Chem. Journ., XIX. 199. 

 II C. R., CXXI. 326, 530. 

 •H These Proceedings, XXX. 423. 



** This preliminary treatment is essential to tlie success of the process. We have 

 not succeeded in getting a sufficiently fine powder by mechanical pulverization. 



