IOO 



might be expected from nitro anethol, could not be obtained by splitting 

 up with hydrochlorid acid. By means of reduction of the nitro com- 

 pound with zinc dust and glacial acetic acid, the oxime C 10 H 13 NO 2 

 (melting point 65 to 66°) could be obtained, which, when split up 

 with dilute sulphuric acid, is converted into the corresponding ketone 

 C 6 H 4 (OCH 3 )CH 2 — CO — CH 3 (d 1,07; n D20O 1,5253), 

 melting point of the semicarbazone 175 . 



The anethol nitroso chloride (melting point 127 to 12 8°) obtained 

 in the usual manner, when heated with alcohol or glacial acetic acid, 

 yields anisic aldehyde; with sodium methylate, the oxime C 11 H 15 N0 3 

 (melting point 4 8°). If the latter, or better its sodium salt, is decom- 

 posed with 10 per cent, sulphuric acid at 8o°, the ketone C u H 14 3 

 is obtained, whose semicarbazone melts at 192° 



C 6 H 4 (OCH 3 )CH — CHCH 3 1 C 6 H 4 (OCH 3 )C — CH — CH 3 



I I -> II \ 



NO CI J / NOH CI 



/ / 



C 6 H 4 (OCH 3 )CHO + NH 2 OH.HCl + CH 3 CHO 



1 C 6 H 4 (OCH 3 )C — CH.CH 3 



II \ _> C 6 H 4 (OCH 3 )COCH(OCH 3 )CH 3 



NOH OCH 3 



Isosafrol nitrite (melting point 12 8°), when treated in a suitable 

 manner, yields entirely analogous bodies as anethol nitrite: /S-nitro- 

 isosafrol, yellow crystals of the melting point 98 ; with soda in alcoholic 

 solution it splits off piperonal oxime, and can be reduced to the 

 oxime (CH 2 2 )C 6 H 3 • CH 2 • C(NOH) • CH 3 , which can be converted 

 into the corresponding ketone (d 1,203; n D20° I >543°)- Melting point 

 of the semicarbazone 163 . Isosafrol nitroso chloride, when treated 

 with sodium methylate, yields the oxime 



(CH 2 2 )C 6 H 3 C-CH-CH 3 



NOH OCH 3 



Analogous compounds are obtained under the same conditions 

 from methyl isoeugenol. 



In a work published by E. Schmidt 1 ) on the same subject, it 

 is shown .that the anethol nitroso chlorides obtained by Til den and 

 Forster's 2 ) process are identic with those obtained by Wallach's 3 ) 

 method. 



x ) Apotheker-Zeitg. 24 (1904), 655. 



2 ) Berl. Berichte 27 (1895), ref. 467. 



3 ) Liebigs Annalen 245 (1888), 251. 



