147 



crystals were obtained which melted at 64°-65.5°. It is insoluble in water, 

 dilute acids and alkalis, but soluble in ether, chloroform, benzol, and alcohol. 

 0.2591 grams gave 10 c. c. of nitrogen at 22.5° and 748 mm. pressure. This is 

 equivalent to 4.39 per cent nitrogen. Calculated for C19H21NO4 equals 4.28 

 per cent. 



To one gram of this diacyl derivative 2 c. c. of a 10 per cent, solution of 

 alcoholic potash were added. Saponification began at once and when all 

 had passed into solution it was acidified and extracted with ether. The 

 ether solution was washed with a solution of sodium bicarbonate and the 

 ether evaporated. The residue after recrystallization from ligroin melted at 

 68.5°-69.5°, and when mixed with the urethane having the same melting point 

 no depression of melting point was observed. From the sodium bicarbonate 

 solution, on acidifying, benzoic acid se])arated and was identified in the usual 

 way. The result indicates that the benzoyl group was attached to oxygen. 



ACTION OF CHLORCARBONICISO.^MYLETHER ON BENZOYL O-AMINOPHENOL. 



Benzoyl o-aminophenol was prepared following the method of Ransom. 

 Two grams of this were dissolved in excess of a 10 per cent, solution of potas- 

 sium hydroxide and 1.6 grams of chlorcarbonicisoamyl ether slowly added. 

 On shaking, an oil slowly separated and this was extracted with ether. From 

 the ether an oily residue was obtained which after several recrystallizations 

 from alcohol formed a white solid melting at 64°-65.5°. A mixture with the 

 supposed isomer had the same melting point. Saponification resulted in the 

 production of benzoic acid and the urethane (m. p. 64°-65.5°). Evidently the 

 benzoyl group in this, as in the former case, is attached to oxygen and must 

 have shifted from its original attachment to nitrogen. 



ACTION OF CHLORCARBONICETHYLETHER ON OXYPHENYLISOAM YLURETHANE. 



One and one-fourth grams of oxyphenylisoamylurethane were dissolved 

 in 4 c. c. of a 10 per cent, solution of potassium hydroxide and to this was 

 added 0.7 grams of chlorcarbonicethylether. A heavy red oil separated. 

 This was extracted with ether and the ether solution washed successively 

 with dilute alkali, dilute acid and water. It was then dried with calcium 

 chloride and the ether allowed to evaporate. The oil did not solidify. It 

 was distilled imder a pressure of 16 mm. at 18o°-200°, the distillate soon 

 solidifying to a yellow crystalline mass. After several recrystallizations 



