( 651 ) 



lo he iho case. If syiniiielrical dinilroaiiisol is troatod lor I wo lioiiis 

 oil llio \vateii)alli willi a iiii\lnr(M)t' IINO^ :(l('iisi(v 1.44) aii<l siilpliiiric 

 acid, Iriiiitroanisol is foniicd in. p. 104". Tlie iiid'Ogroiip iiid-odiicefi 

 iiilo lliis siihslaiice is moltilo and easily rej)lace(l b}- OH, ()('H.,, NH.^, 

 NHC'H., ele. If liie N().^ gi-oiip is replaced Ity OH diiiilrognaificol is 

 tbi-nied m.p. 121^ By Ireafinenl witii aicoiiolic metiiylaniine, nietlivl- 

 amido-diiiitroaiHsol is formed m.j). ll^S", which is coiiv<M-ted h\- iiili-ic 

 aciii of i.52 sp. u'i'. into oxynielliyl-<liiiili'opheiiyl-inelhylnilrainiiie in.p. 

 118^ already obtained by Okimaux and I.Kt'i'.VRK ^) by nifi-alioii of 

 diniethyl-orthoanisichiie. This i>oos lo prove that the uilrogroiip in 

 regard to the OCH.,-gronp has been introduced into tiie oi'lho place 

 and that, therefore, the eonstitntion of Irinitroanisol is i-ejireseiited by 

 C„H, OCH3 (NOJ,. 1. 2. 8. 5. 



H' trinitroanisol is treated with a solution of Na OCH, in methyl 

 alcohol the NO^ groii|) 2 is replaced by OCH3 and the diinethylelher 

 of diiiitropyrocatechiiie is formed, m.p. 101°. Treatment with alcoholic 

 ammonia yields dinilroanisidine C, H., (OCH3) NH._, (NO.,)^ 1. 2. 3. 5, 

 m.p. 174; with aniline and aethylamine are foi-med coni}»ounds 

 melting respectively at 155° and 123°. 



If trinitroanisol is nitrated with a mixture of niti-ic acid of 1,52 

 sp.gr. and sulphnric* aeid a tetranitroanisol is formed m.p. 154''. On 

 treatment with 2 mols. of Na OCHs, this substance is converted into 

 crystals which melt at 165' and assume a puri)le-brown color when 

 ex{)oscd to light. 



Analysis shows that two NO. ^ groups are replaced by OCH.,. L()rln{; 

 Jackson^) by treating symmetrical tribi-omodinitrobenzenc with 3 mols. 

 of Na OCHj has pre[)are(l a com[)ouiid with the same properties as 

 the above mentioned; he however considered that he had obtained 

 the diinethylether of dinitrorcsorcijiol. The latter substance melts 

 however, according to FRKYss')and Mki.doi.a ^) at 154°, whilst Mkkkum 

 Tkkwoot ') and 1 have found 157'. It is therefore very probable 

 that LoKiXG Jackson has been dealing with the trimethvlether of 

 dinitrophloroglucinol as, on treating symmetrical tribi-omodinitrobenzene 

 with Na OC^H^, all three Hr-aloms may be re|>laced by OOJl. "). 



That the compound obtaine<i fnun teli-aniti-oauisol and NaOCII^ is 

 really identical with that from svmniclrical Iribroinodinitrobcnzene 



ij Compl. Rond. 112. 727. 



~) Amor. Cllioiu. .loiirn. 13. ISO. 



"•) Cenlr. BlalL 1901. I. 7:W. 



*) Proc. Chem. Soc. 17. i:n. 



5) Roc. 21. 288. 



^) Amer. Chem. Jouin. 21. 512. 



