lOO 
For the purpose of ascertaining the constitution of apiol, for which, 
according to the work by Ciamician and Silber^), hitherto only the 
folio wine: two formulse 
CH, .CH:CH 
came under consideration: 
CH, .CH:CH, 
/ \ 
O 
CH2-O 
OCHe 
OCH, 
OCH.. 
O — CH. 
Thorns started from isoapiol, or respectively from a degradation- 
product of this body, a propyldimethoxy phenol. The methyl ether 
of this phenol, when treated suitably with dilute nitric acid, yields a 
nitro- product in addition to a quinone. Contrary to the process 
mentioned for dihydroasarone, no elimination of a methoxy-group has 
here taken place, but the entry into the free para-position towards tlie 
propyl-group has occurred. The quinone which occurs in addition, is 
isomeric with the one formed from clihvdroasarone. The followino- 
formulae may illustrate this more clearly: — 
C3H, 
0CH3 CH3O 
OCH. 
OCH3 O 
OCH. 
NO. 
OHi^^OCH3 
propyldimethoxy phenol methyl ether 
nitro product 
qumone 
By means of these results the question of the constitution of pro- 
pyldimethoxy phenol (and consequently also of apiol) could be decided. 
For this purpose there were produced, by substitution of the hydrogen 
atom of the OH -group by an ethyl- and a propyl-group, a propyl- 
dimethoxy-ethoxy-benzene, and a propyl-dimethoxy-propyloxy-benzene, 
and each of these compounds was converted by means of nitric acid 
^) Berichte 23 (1890), 2293. 
