quinone-like formulae, in which the methyl of the methoxyl-group, or 
respectively an H-atom in the a-position of the side-chain, enter into 
the para-position: 
CH3O . <( y . CHBr . CHBr . CH3 
CH3 CH3O 
0:<' X X ):CBr.CHBr.CH3. 
^CHBr.CHBr.CH. 
Apiol. Products due to the action of nitric acid on phenol ether 
have recently served H. Thoms^) for establishing the constitution of 
apiol. For the more detailed study of the interesting examination 
we must go back to an earlier work by H. Thoms and J. Herzog^), 
In the latter these chemists showed that dihydroasarone, when treated 
with nitric acid, yields, in addition to a known quinone, also a nitro- 
body, in which the nitro-group occupies the para-position towards the 
propyl -group. There has consequently taken place an elimination of 
the methoxyl-group situated in i, 4-position towards the propyl-group 
in the dihydroasarone molecule: 
CH3O 
CH: CH . CH. 
OCH. 
C • C • C H3 
OCH. 
OCH. 
asarone 
CH3O 
OCH. 
dihydroasarone 
and 
CH30 
C • C H2 • C H3 
OCH. 
NO, 
nitro-product 
( I ) propyl- (2,5) dimethoxy- 
(4) nitrobenzene 
C Hg • C • C H3 
^) Berichte 36 (1903), 17 14. 
2) Ibidem 36 (1903), 854. 
