28 ADULTERATED DRUGS AND CHEMICALS. 



for the first time acetanilid and benzanilid, by the action of acetic 

 anhydrid and benzoic anhydrid, respectively, on anilin. This same 

 worker" had made benzanilid seven years before by the interaction of 

 benzoyl chlorid and anilin. 



In 1854 J. Fritzsche began to study the action of nitric acid on 

 phenol. His first results were presented to the St. Petersburg 

 Academy of Sciences November 6, 1857.* In this communication he 

 reported the preparation of ortho-nitrophenetol by the action of ethyl- 

 iodid on a silver salt of ortho-nitrophenol. The ester was extracted 

 and purified by treating the mixture with ether, evaporating the sol- 

 vent, and distilling the resulting reddish-yellow fluid. The product 

 thus obtained was nearly odorless, almost insoluble in water, but 

 readily soluble in alcohol and ether. Boiling caustic potash solution 

 decomposed it with difficulty. 



The following }^ear c the same worker discovered and described 

 isonitrophenic acid (para-nitrophenol) and some of its derivatives. 

 The derivative of particular interest in this connection is its ethyl 

 ester, para-nitrophenetol, prepared as was the ortho-nitrophenetol 

 above. Para-nitrophenetol he described as a colorless crystalline body 

 possessing an agreeable aromatic odor, nearly insoluble in water, 

 soluble in ether and alcohol, and melting at 57 to 58 C. 



Nothing of importance appeared again until A. GrolH announced 

 the preparation of ortho-amidophenetol from ortho-nitrophenetol. 

 The latter was prepared by dissolving potassium nitrophenolate and 

 ethyl bromid in from 3 to 4 parts of alcohol and heating the mixture 

 for a number of hours in a sealed tube at from 140 to 160 C. 

 Ortho-amidophenetol was made by treating ortho-nitrophenetol with 

 metallic tin and hydrochloric acid. From this time forward the nitro- 

 phenetols were well known to organic chemists, being frequently 

 employed by them in their research work, and probably in the indus- 

 trial world. Para-nitrophenetol was used by R. Schmitt and R. 

 Mohlau" in their investigation on azoxy-azo- and hydni/o-phenetol, by 

 Schmitt/ during his study of the constitution of the dichlorazophe- 

 nols, and R. Mohlau in his dissertation? very fully describes ortho- 

 nitrophenetol. The latter, in his study of ortho-diamidodiphenetol, 7 ' 

 fully sets forth that the phenetols were common property. 



Comp. rend., 1845, 20: 1031. 



''St. Peters)). Bull. Classe phys. math., 1858, 16: 161; J. prakt. Chem., 73: 293; 

 Cheni. Central!). (2), 8: 171. 



St. IVUTsb. Bull. Classi- phys. math., 1859, 17:145; J. prakt. Chem., 7.">: L':.7: 

 Ann. (Liebig), 110: l.V>: .Fahn-sh. i Lifhig and Kopp), 11:407. 



^ J. prakt. Chem., 1875 (2), 12: 207. 



J. prakt. Chem., 1878 (2), 18: 198. 



/ J. prakt. Chem., 1879 (2), 19: 312. 



g Dissertation, Freiburg, 1879, i, B. 27, ff, through J. prakt. Chem., 1880 (2), 21: 318. 



* J. prakt. Chem., 1879 (2), 19: 381. 



