56 KANSAS ACADEMY OF SCIENCE. 



it was evident that the reaction was beginning and then cooling it as 

 soon as possible. In this way almost no black decomposition products 

 and relatively more of the mono-chlorbenzene was obtained. In the 

 fractional distillation, a part distils over below 90°. This was used in 

 the next chlorination. The next fraction contains mono-chlorbenzene, 

 b. p. 132". At higher temperature, small amounts of dichlorbenzene, 

 b. p. 172^, and of 1, 2, 3, 4-tetrachlorbenzene were obtained ; and 

 finally in one case, when the chlorination was carried too far, some 

 higher distillations were obtained, even up to 300°; but no other pure 

 compounds were separated. It was necessary to repeat the fractional 

 distillation at least seven times to separate the compounds. 



Para-nitrochlorbenzene was next prepared (Riche A. 121, 357), 

 by nitrating the chlorbenzene with fuming nitric acid at the tempera- 

 ture of ice-water. Both the ortho and para compounds are formed. 

 At first the para compound was obtained pure by repeated crystalliza- 

 tions, but it was found later that an almost complete separation could 

 be made by means of a Buchner funnel and the suction-pump. The 

 ortho compound contains a considerable quantity of impurity, and is 

 a liquid, and if pure it should melt at 32.5'^. The para compound be- 

 ing solid, m. p. 83°, remains on the filter. 



Paranitro-phenetol was then obtained ( C. Willgerodt, Be. 15, 

 1002 ) by heating a mixture of 300 cc. alcohol, 150 cc. water, 10.5 

 g. potassium hydroxid, and 30 g. j^-nitrochlorbenzene for thirty-six 

 hours in a flask with a return condenser. The product obtained, 

 after diluting with water and filtering, was purified by distillation 

 with steam. The unchanged ;?-nitrochlorbenzene distils over first, 

 followed by the /»-nitrophenetol. A solid dichlorazoxybenzene, melt- 

 ing at 155°, and /?-nitrophenol in solution remain in the flask. 



Paraazoxyanisol was next prepared. Six g. sodium, 60 g. methyl 

 alcohol, and 16 g. j9-nitrophenetol ( Schenck, Zeits. Phys. Chem. 25, 

 346), were sealed in tubes and heated for five hours at 110°, in the 

 bomb furnace. The product, treated with alcohol, left a solid, which, 

 when crystallized from chloroform, melted at 114 , and passed its 

 transition point at 134°. As no microscope with heating stage was 

 available, the double refraction of the paraazoxyanisol could not be 

 observed by us. 



