410 PROCEEDINGS OP 'tHE AxMERICAN ACADEMY. 



possible that the compounds formed by such a replacement might have 

 been overlooked among the secondary products of some of these 

 reactions, or might be formed under other conditions, we have carried 

 through our experiments. In fact, one of them has proved that, when 

 sodic methylate acts upon chloranil, a reduction takes place, but the 

 hydrogen, instead of replacing chlorine, reduces part of the chloranil 

 to the corresponding tetrachlorhydroquinonCo The work with clilor- 

 anil, therefore, did not throw light on the replacement of bromine by 

 hydrogen in tribromdinitrobenzol, because of the presence of the two 

 atoms of quinone oxygen, which seized upon the hydrogen before it 

 could replace the halogen. In the mean time, however, our experi- 

 ments have led to interesting results of another sort, which are 

 described in this paper. 



The action of potassic phenylate on chloranil was the first selected 

 for study, and we found that, if the substances were mixed in the 

 proportion of two molecules of the former to one of the latter, the 

 product was dichlordiphenoxyquinone, CgCl2(OCgHj2C)2) which melts 

 at 243°, and gives a hydroquinone melting at 197°-198° when treated 

 with reducing agents. With the object of replacing the two remain- 

 ing atoms of chlorine we next treated the dichlordiphenoxyquinone 

 with aniline, but instead of acting on the atoms of chlorine this 

 reagent attacked the phenoxy groups, giving dichlordianilidoqiiinone 

 and phenol, behaving in this respect in the same way as dichlordime- 

 thoxyquinone, which, Kehrmann* found, was converted by treatment 

 with aniline into dichlordianilidoquinone. This action we found 

 was the normal one for our substance ; for example, sodium malonic 

 ester gave with the dichlordiphenoxyquinone the dichlorquinonedi- 

 malonic ester melting at 132° discovered by Stieglitz f ; and, strangely 

 enough, this indirect method of preparing the substance gives a better 

 yield than the direct action of sodium malonic ester on chloranil, for 

 while Stieglitz by this latter method obtained only about 10 per cent, 

 our yield was as high as 27 per cent. The beautiful bright blue 

 sodium salt CgCl202[CNa(COOC2H5)2]o was obtained, and analyzed ; 

 it is stable for a malonic ester salt. The " deep pure violet color, 

 resembling exactly a concentrated solution of potassium permanganate," 

 obtained by Stieglitz upon the addition of sodic hydrate to the sub- 

 stance, is due, according to our observations, to some decomposition of 

 the salt brought about by an excess of the alkali. The solution of 

 the pure salt has the full blue color of aniline blue. 



* Journ. Prakt. Chem., [2.], XL. 370. t Am. Chem. Journ., XIII. 38. 



