JACKSON AND TORREY. — AN ORGANIC OXIDE. 153 



was treated with a solution of sodic ethylate, and the hemiacetal formed 

 decomposed with hydrochloric acid, when the crude quinone thus obtained 

 melted at 100°-10o°, and recrystallization did not raise the melting 

 point above 105°; it is, therefore, dichlordiethoxyquinone, which melts at 

 104°-105°, and the ethoxy group has replaced the methoxy group. 

 These experiments make it probable that any alcohol radical can be re- 

 placed by any other in these substituted quinones, if the substance is 

 treated with the proper sodic alcoholate,* and therefore that the isolation 

 of mixed hemiacetals containing one radical on the ring and another in 

 the acetal part of the molecule would be a matter of great difficulty. 

 These experiments were in fact undertaken to explain the failure of our 

 work on such mixed hemiacetals and acetals, which we had tried to i)re- 

 pare, because we hoped the conversion of them into the corresponding 

 oxides would throw some light on the constitution of these latter bodies. 

 Our attempts to make the dimethoxyquinonediethyldibenzoylacetal led 

 to the diethoxydiethyl body as the principal product, but probably a 

 small quantity of the mixed acetal was also formed, as the crude product 

 began to melt at 130°, and it was only after many crystallizations that 

 the pure diethoxydiethylacetal melting at 170° could be obtained. 



Action of Isoamylamine on the Oxide C6Cl20CH30(OCOCeH5)20CH3. 



Three grams of the oxide were dissolved in hot benzol, and 4.5 grams 

 of free isoamylamine were added with constant stirring. A reaction 

 took place at once with the formation of a yellow precipitate so abun- 

 dant that the contents of the beaker became almost solid. As this yellow 

 substance is very unstable, we devoted our attention at first to the pro- 

 duct of its decomposition, which was more easily obtained and purified. 

 To bring about the decomposition the mixture was heated gently, when 

 the yellow color changed to a purplish red, and the greater part of the 

 solid went into solution, but was deposited as the benzol cooled. The 

 purplish red solid thus obtained was washed with benzol, and then with 

 water, after which it was purified by recrystallization from hot benzol, 

 to wliich a very little methylalcohol had been added. It was then dried 

 at 100° and analyzed with the following results : — 



* Replacements similar to these have been observed with other classes of bodies 

 by Friedel and Crafts, Ann. Chem., CXXXIII. 208; Israel, Ibid., CCXXXI. 220; 

 Isbert, Ibid., CC XXXIV. 160 ; Peters, Ibid., CCLVII. ,353 ; Purdie, Per. d. cliem. 

 Ges., XX. 1554 ; Bertoni, Gaz. Ciiim., XII. 435, XV. 361 ; and Gattermann and 

 Ritschke, Ber. d. chem. Ges., XXIII. 1738 (1890). 



