— 6o — 
isobutyric acid. Eugenol, already detected by us in laurel oil on a 
previous occasion i), was also found by Mo lie in the oil examined 
by him, and that in quantities of i,7% as free eugenol, and 0,4 ^/q 
as esterified eugenol. The author was unable to detect the presence of 
aldehydes and ketones in the subject of his examination. By saponifying 
the oil from which the free acids and phenols had been removed with 
alcoholic potash liquor, the acids originally present in the form of esters 
were converted into their potassium salts, and from these were produced 
compounds of the acids capable of analysis. Acetic acid was detected 
with certainty; in addition to this, valerianic and caproic acids are 
probably present in the form of their esters, in an approximate mixture- 
proportion of 40^/0 valerianic and 60 ^/q caproic acid. In addition to 
these acids, he also isolated 0,07^/0 ^ monobasic solid acid C^o^i4.^2 
whose melting point lay at 146° to 147°. This acid was strongly 
attacked by potassium permanganate; of bromine it absorbed two atoms. 
This last acid is probably not present in the original oil, but is only 
formed when the oil is treated with alcoholic potash liquor. Presumably 
a genetic relationship may exist between this acid and camphene. 
Pinene, which Wallach^) had already discovered in laurel oil, could 
only be detected by Molle when he used oil for the reaction, which 
had not yet been treated with alkali. On fractional distillation of the 
oil freed from acids and phenols, cineol was found in the portions 
passing over from 170° to 180^, which represent about 50^/0 of the 
oil. This had also been established previously by Wallach. Molle 
was unable to detect methyl chavicol whose presence was suspected 
in the portions boiling above 180°. The fraction passing over from 
212° to 230° contained geraniol, which was identified as such by 
oxidation into citral and conversion into citryl-/3-naphthocinchoninic 
acid. From the same fraction, terpinene Qo -^le could be obtained by 
splitting off water, and terpin hydrate by treatment with dilute sulphuric 
acid. In the high-boiling portions of laurel oil there may possibly be 
present, in addition to sesquiterpenes, also sesquiterpene alcohols, but 
no characteristic derivatives of such could be obtained. 
Experiments made on the occasion of this examination with regard 
to the reduction of cineol, showed that for this purpose only hydriodic 
acid was useful. Molle obtained the best results by one hour's heating 
to 220° to 225°, in a sealed tube, with metallic mercury as the iodine- 
binding agent, when a hydrocarbon Qo^iS' ^^^.med "cineolene", and a 
polymeric hydrocarbon (C^o -^16)11 were formed. Cineolene boils at 165° 
to 170°, is optically inactive, and has the specific gravity 0,8240 at 18°; 
nj^= 1,45993. This body does not absorb bromine; if it is attempted 
1) Report April 1899, 31. 
2) Liebig's Annalen 252 (1889), 95. 
