JACKSON AND TORREY. — AN ORGANIC OXIDE, 149 



made from fifty grams of phenol and twenty-five grams of potassic 

 hydrate. The product was washed thoroughly with water, then with 

 alcohol, and finally with benzol or ether. It was not recrystallized. 



The dichlordiphenoxyquinone was then converted into the dichlor- 

 dimethoxydimethylhemiacetal by adding twenty grams of it in small 

 portions at a time with constant agitation to the sodic methylate made 

 from five grams of metallic sodium and 120 c. c. of methyl alcohol. It 

 was found best to carry on this reaction in a flask. The mixture was 

 then warmed on the water bath, and afterward allowed to stand for 

 a short time to permit the separation of the sodium salt of the hemiace- 

 tal, which was sometimes hastened by the addition of a little ether. The 

 salt collected on a filter was washed with ether and with a very little 

 alcohol, or better a mixture of alcohol and ether. 



The dibenzoylacetal was next made by treating twenty-five grams 

 of the dry salt suspended in a small quantity of methyl alcohol with 

 twenty-two grams of benzoylchloride. The reaction was completed by 

 warming the mixture for a short time on the water bath. The product 

 usually contained, in addition to the colorless dibenzoylacetal, a red sub- 

 stance, probably dichlordimethoxyquinone, which was most easily re- 

 moved by treatment with warm sodic hydrate, as this reagent converted 

 the red substance into sodic chloranilate, but did not act on the acetal. 

 The chloranilate was then washed out with hot water, leaving the acetal 

 pure enough for our purposes. 



The dry acetal was next saponified by heating it for fifteen or twenty 

 minutes in a flask with a return condenser with sulphuric acid of specific 

 gravity 1.44. The contents of the flask were then allowed to cool, and 

 after the addition of a little water the solid product was filtered out, and 

 washed with hot water to remove the chloranilicacid always formed in the 

 reaction. The white oxide left was then purified by one or two recrystalliza- 

 tious from chloroform and alcohol. The yield of oxide was a little under 

 80 per cent of the amount which should be obtained from the acetal. 



The processes which are carried on in this preparation are represented 

 by the following reactions : — 



C,C1,0, + 2 NaOCgHj = C,C1.3(0CeH,),0, + 2 NaCl. 

 C6C1,(0CJ45)20, + 4 NaOCHs = C,CL(OCH,)„(ONa)o(OCH3)2 



+ 2 NaOCgH,. 

 C6Cl2(OCH3)2(ONa)o(OCH3)2 + 2 C.H.COCl = 



2 NaCl + CsCl2(OCH3)2(OCOC6H,)2(OCH3)2. 

 C6Cl,(OCH3),(OCOC,H3),(OCH3), + HoO = 



C,CloOCIl30(OCOC,H,),OCH, + 2CH3OH. 



