6 



— 132 — 



Since for parsley apiol the formula of a i-allyl-2,5-dimethoxy- 

 ,4-methylene dioxybenzene had been established 1 ), there could only 



come under consideration for dill apiol which Thorns had found in 

 matico oil i-allyl-5,6-dimethoxy-3,4-methylene dioxybenzene, of which 

 the correctness has been demonstrated by Thorns 2 ). The argumentation 

 follows closely on the lines of the one previously given for parsley 

 apiol, and, like the latter, culminates in the displacement of two alkoxy- 

 groups in the para-position, with formation of a quinone. 



Conjointly with A. Biltz, Thorns 3 ) publishes a communication 

 on the relationship between safrol, eugenol, and asarone. From dihy- 

 drosafrol (obtained by reduction from isosafrol with sodium and 

 alcohol), there could be produced by treatment with glacial acetic 

 and nitric acid, a nitro- compound of the formula 



H O-CH, 



C 3 H 7 < > o 



N0 H 



of the melting point 3 6°, whose methylenedioxy-group could be split 

 up with aluminium chloride. By etherifying with dimethylsulphate the 

 mixture of isomeric phenols produced, Thorns and Biltz obtained 

 a nitrodihydromethyl eugenol of the melting point 8i°, which was 

 identic with the one formed from isoeugenol. On reduction with 

 aluminium amalgam, the nitrodihydrosafrol was converted into the 

 little stable corresponding amino compound of the melting point 24 ; 

 when nitrated further, the nitro-product yielded a dinitrodihydrosafrol 

 from which a diamino body was produced by means of aluminium 

 amalgam; with ammonium sulphide a nitroamino- compound was formed 

 in which the second nitro -group was reduced, as after elimination 

 of the amino -group the original product of the melting point 3 6° 

 was again recovered. On saponification of the nitrodihydromethyl- 

 eugenol with aluminium chloride there were formed two isomeric 

 nitrophenols of the melting points 52 and 7 8°; the former was ethyl- 

 ated with ethyl iodide, the ether reduced into the amine, and the latter 

 oxidised by means of bichromate mixture into the quinone 



H O 



C Q H 7 < )OCE 



O H 



J ) Berl. Berichte 36 (1903), 1714. — Report October 1903, 99. 



2 ) Arch. derPharm. 242 (1904), 344. 



3 ) Arch, der Pharm. 242 (1904), 85. 



