432 PROCEEDINGS OF THE AMERICAN ACADEMY. 



tatively, slowly in the cold, but quickly on warming. The ease with 

 which it is attaclied by dilute acids is its most striking property. 

 Continued boiling witli water or with dilute alcohol or glacial acetic 

 acid brings about the same decomposition, as does also treatment of 

 either the free substance or its sodium salt with benzoylchloride in 

 a sealed tube at 100°, methyl benzoate being the secondary product. 

 Acetic anhydride decomposes it in the same way, but more slowly ; 

 on the other hand, neither methyl nor ethyl iodide acts on the sodium 

 salt or the free substance. The formation of the benzoic ester of 

 the substance is described below. 



The hemiacetal is a weak acid, forming with sodic metliylate the 

 wliite crystalline sodium salt, the method of preparation and analyses 

 of which have been given above. This salt is soluble in water or 

 alcohol, insoluble in ether. With argentic nitrate a white non- 

 crystalline silver salt is formed, which is insoluble in water, and easily 

 decomposed. 



Action of Sodic EthyJate on Dichlordiplienoxyquinone. — Dichhrdie- 

 thoxyquinone Diethylhemiacetal, C6Cl9(OC2H5)2(Ori )2(OC2Hs)2. 



In order to study this action 10 grams of dichlordiphenoxyquinone 

 were treated with an alcoholic solution of little less than four equiva- 

 lents of sodic ethylate, which was made by treating 2.5 grams of metal- 

 lic sodium with 60 c.c. of absolute alcohol. When the sodic ethylate 

 was first added there was no apparent action, but on standing, even in 

 the cold, the red color of the dichlordiphenoxyquinone gradually disap- 

 peared, and a white crystalline sodium salt was formed. After warm- 

 ing gently on the water bath to finish the reaction, the solution was 

 filtered, the salt washed with alcohol, dissolved in water, filtered again, 

 and then dilute sulphuric acid added in excess, which gave a bulky 

 white precipitate. This was filtered off, washed with water, alcohol, 

 and then with water again. In order to purify the substance further, 

 it was dissolved in dilute sodic hydrate, filtered, precipitated again with 

 dilute sulphuric acid, and washed thoroughly, as above. This treat- 

 ment was repeated until finally the substance was perfectly white, and 

 did not change color when washed with alcohol and ether, and then 

 dried for a short time over sulphuric acid and paraffine. The product 

 was analyzed with the following results : — 



I. 0.2205 gram of the substance gave on combustion 0.3802 gram of 



carbonic dioxide and 0.1304 gram of water. 

 II. 0.2017 gram of the substance gave by the method of Carius 0.1614 

 gram of argentic chloride. 



