144 ’ REPORT OF SCHIMMEL 8 Co. APRIL 1914. 
Anethol, when reduced with hydrogen under a pressure of 50 atm. in the presence 
of reduced nickel, afforded at 95° dihydroanethol (b. p. 212 to 214°; dooo 0,9462). 
Hydrogenation of the dihydroanethol at 200° led to hexahydropropylbenzene (b. p. 160°). 
Hence the methoxyl-group was split off. Treated similarly, eugenol and isoeugenol 
afforded dihydroeugenol (b. p. 246°). When the reduction-process was continued a 
mixture of hexahydroanethol and octohydroeugenol resulted. Eugenolmethylether 
affords the dihydromethylether which, when further reduced, yields octohydroanethol, 
a methoxyl group being split off. Safrol and isosafrol yield dihydrosafrol (b. p. 228 to 
230°) and, upon further reduction, in all probability an isomeric hexahydroanethol. © 
Thymol. K. Fries, W. Gross-Selbeck and O. Wicke'), in a voluminous paper, com- 
municate the results of their researches into the o-pseudobromides of thymol and 
o-isopropylphenol, and their conversion into cumarane derivatives. The manner in 
which the numerous preparations were obtained, and the preparation of characteristic 
derivatives are accurately described. 
Methylthymol. In a communication by E.Clemmensen?) on a general method 
of reduction of the carbonyl group of aldehydes and ketones into the methylene group, 
we find a description of the preparation of p-methylthymol from p-thymotine aldehyde. 
25 grams of the aldehyde, 150 grams 
WOES WA Ne of amalgamated zinc and 400 cc. of 
H;C DoH <-— een DASt dilute hydrochloric acid (1:1) were 
\—— —— heated for 3h ith f t ad- 
CH(CH,): CH(CH,)» eated for ours with frequent a 
dition of further quantities of acid 
of the same strength. The reaction 
product, when driven over by steam, solidified into a white, crystalline mass, which 
was purified by distillation (b. p. 250 to 250,5° at 745 mm.) and recrystallisation from 
light petroleum. Pure p-methylthymol melts at 70°. It has a pleasant odour, which 
differs altogether from that of thymol. ) 
p-Methylthymol. p-Thymotine aldehyde. 
Phenol allylethers. In our last April Report (p. 144), we mentioned a paper 
by L. Claisen on the conversion of phenol allylethers into C-allylphenols. Claisen 
and O. Eisleb?) have recently published a very detailed treatise on the same subject, 
from which we make the following excerpts which specially concern our particular 
sphere of interests. Conversion takes place as soon as the allylether is heated; as 
a rule a temperature below b. p. suffices to bring it about; only occasionally is it 
necessary to heat to b.p. A temperature of between 230 and 250° may be taken as 
the most favourable average for the conversion. The allylether of ordinary eugenol 
(b. p. 140° at 9 mm.; dis0 1,024) affords at b. p. immediately and at 200° within about 
half an hour, about 70 p.c. o-allyleugenol (0, p-diallylguajacol), a water-white oil with 
an odour resembling that of eugenol, but much fainter than the latter: b. p. 149° 
(10 mm.), diso 1,036. In the process of conversion of guajacol allylether o-eugenol 
(o-allylguajacol) is, in fact, formed. o-Eugenol allylether boils at 128° (10 mm.). When 
o-eugenol is treated with potash in the warm the solid propenyl derivative, o-2soeugenol 
(o-propenyl guajacol) is formed: m.p. 78°. This body is identical with that obtained 
from o-vanillin and ethyl iodide by Pauly and von Buttlar*). It is possible greatly to 
1) Liebigs Annalen 402 (1914), 261. — 2) Berl. Berichte 47 (1914), 62. — #8) Liebigs Annalen 401 (1913), 
21. — 4) Ibidem 3838 (1911), 282.. ORF =: 
ae Rs es 4 
