PHENACKTIN. W J'. 



By allowing finning nitricacid to act on phenetol. ( 'ahoin^ ' obtained 

 a solid and a liquid body; the former he called dinitrophenetol and 

 the latter inononitroplirnetol. K. .1. Hal lock'' repeated these ex peri 

 inents and ohtaiiuMl two similar bodies. He sa\ 83 



The solid, when purifiod by repeated recrystalli/atioiifl, both from arid and from 

 alcohol, was proved by an ultimate analysis to In- a nmmmitrophenetol. Its melt- 

 ing point, 58 G., and other physical properiies coincide \\ith that of para- 

 mononitrophenetol, prepared by Frit/schc in isr>s by the action of iodid of rthyl 

 upon the silver salt of para-nit rophenol. 



H. Andreae c in his excellent communication of nitro-ortho and 

 nitro-pani-azophenetol shows that he was well acquainted with both 

 the para- and the ortho-nitrophenetol. C. Willgerodt' 7 gave a new 

 method for preparing para-nitrophenetol, as indicated bv the follow- 

 ing equation: C 6 H 4 (NO 2 )Cl+C a H 5 OH-C 6 H 4 (NO 2 )OC 8 H 5 +HCl. II. 

 Kolbe c gave additional methods for preparing these products. Other 

 useful papers published bearing on these products were contributed 

 by J. Berlinerblau/ C. Liebermann and St. Kostanecki, ^ and C. 

 Willgerodt and M. Ferko. A 



The next step involved in the production of the phenacetins is the 

 conversion of the nitrophenetols into the amidophenetols. This is 

 usually done by the well-known nascent hydrogen process. 



Ortho-amidophenetol was first given to the world by A. Groll ' in 

 1875. The same compound was produced by M. Forster^ in 1880 and 

 by J. Berlinerblau-^ in 1884. Meta-amidophenetol was well known to 

 Berlinerblau/ and Ph. Wagner, * and undoubtedly to other organic 

 chemists in the early eighties. The discovery of para-am idophenetol 

 is generally credited to the American chemist, E. J. Hallock.'' but R. 

 Schmitt's ' work on the constitution of the dichlorazophenols shows 

 that chemists were well acquainted with this compound before the pub- 

 lication of Hallock's article. It was well known to Liebermann and 

 Kostanecki^ in 1884. 



The process described in the phenacetin patent for the manufacture 

 of para-phenetidin was old and well known prior to the date when the 

 patent was granted 1889. Substantial!'- the same method was 

 described in 1884 by H. Kflhler. 



Aim. Chim. Phys., 1849 (3), 27: 4;r>. tfBer. d. diem. <;>.. 1884, 17 S76. 

 ''Am. Chera. J., 1879, 1: 271. A J. ,,,-akt. Chem. !**; (2), 38: 152. 



<-J. prakt. Chem., 1880 (2), 21: 318. J. prakt. Chem. 



</Ber. d. chem. Ges., 1881, 14: 2636; ^J. prakt. Chem. 



ibid., 1882, 15: 1002. U. prakt. Chem. 



^J. prakt. Chem., 1883 (2), 27: 424; M. prakt. Chem. 



ibid. (2), 28: 62. J. prakt. Chem. 



/ J. prakt. Chem., 1884 (2), 30: 97. 



1875 '2), 12: 207. 

 1880 (2), 21: 341. 

 1885 (2), 32: 70. 

 1879 (2), 19: 312. 

 1884(2), 29:257. 



