XI, A, 2 Brill: Diethylsuccinosuccinate, II 67 



Kehrman " prepared dichlordiethoxyquinone melting at 

 95-96° by treating an alcoholic suspension of chloranil at 

 a temperature of 50° C. with a 1 per cent solution of alcoholic 

 potash. Later ^* he claims to have prepared two modifications 

 which he calls "allo-isomers," by treatment of chloranil with 

 alcoholic potash at different temperatures. 



His so-called a-compound melted at 107-108° C. Kehrman pre- 

 pared this isomer by treating an alcoholic suspension of chloranil 

 with alcoholic potash at a temperature near the boiling point of 

 alcohol. It was obtained in the form of crystalline needles. The 

 /8-compound melting at 98° was formed by treating an ice-cooled 

 alcoholic suspension of chloranil with a 1 per cent alcoholic 

 potash solution. By this method he claims to have prepared the 

 /8-compound entirely free from the a-modification. In his pre- 

 paration of the a-modification he freed it from the /3-modification 

 by making use of their difference in solubility in alcohol, the 

 a-compound being more soluble in cold alcohol, but less soluble 

 in hot than the y8-compound. These compounds could not be 

 transformed, the one into the other, by heating alone, with 

 alkalies or with acids. 



I have undertaken to make these two modifications in the 

 manner described above, but without success in the case of 

 the a-compound. Even with the most minute attention to the 

 details of his method, no a-compound could be obtained, the 

 /8-compound resulting in every trial, and by repeated crystal- 

 lization from alcohol no separation of this modification from the 

 /3-modification was attained. 



The compound used here was prepared by treating an alcoholic 

 suspension of chloranil with alcoholic potash at a temperature 

 of 50° and later warming to boiling." By repeated crystalliza- 

 tion from alcohol, glacial acetic acid, and ether a platelike crys- 

 talline body was obtained melting at 96° C. 



The alcoholic solution is chrome yellow, with a refrangible 

 band in the color region heading at 1/A=2,420 and a second 

 deeper band in the ultra-violet region heading at 1/A=3,350. 



Attempts were made to prepare the oxime by treating a solu- 

 tion of the quinone with free hydroxylamine, but without suc- 

 cess. Kehrmann ^* records unsuccessful experiments to prepare 

 the oximes of tetra-substituted quinones by various methods 



"Journ. f. prakt. Chem. (1889), 39, 318. 



"Ibid. (1889), 40, 365. 



" Kehrman, loc. cit. 



"Ber. d. deutsch. chem. Ges. (1888), 21, 3315. 



