760 
consists of propionic acid, the calcium salt of which contains 21.5 °/, 
Ca. On heating the ammonium salt an amide with a melting point 
of 78° was obtained which, on mixing with propion-amide, produced 
no depression of the melting point. 
The hexylene alcohol obtained from tea-oil might therefore be 
hexene-3-ol-6 of the formula CH,. CH, CH: CH. CH,. CH,OH. A 
hexylene alcohol has been obtained by H. WarBauM *) from Japanese 
peppermint oil to which after investigation he attributes the structure 
of a g-y-hexenol. This alcohol is presumably the same as that extracted 
from tea oil. 
On oxidation with potassium permanganate the 8-y-hexenol gives 
propionic acid as principal product. With chromic acid a hexylene 
acid is obtained. The «-naphthylurethane prepared from the alcohol 
melts at 80°, while the melting point of the silverssalt of the acid 
phthalic acid ester melts at 126°. On treatment with bromine only 
70°/, of the quantity required by theory is absorbed. 
It is true that the melting points of WarBaum’s silver salt and 
my own do not agree, but the other properties of the tea-alcohol 
justify the assumption that the latter to a great extent consists of 
B-y-hexenol. I am, however, for the moment unable to explain why, 
on oxidation with potassium permanganate, an acid was obtained 
previously, the calcium salt of which contained only 18.6 °/, of 
calcium. The acid on that occasion was not distilled, as the quantity 
available was too small, and may have contained, for example, 
hexylic acid, by which the calcium content of the propionic acid 
formed would be lowered. Finally it may be possible that the 
heating of the crude oil with alkali in order to remove the methyl 
salicylate, has caused a shifting of the double bond. 
This research, as well as the investigation of the other constituents 
of the tea-oil, is being continued ’”). 
Postscript. 
Since the above paper was communicated, the firm Messrs. 
SCHIMMEL and Co. of Leipsic sent me at my request a small quan- 
tity of the unsaturated alcohol prepared from Japanese peppermint 
oil, for which I desire herewith to express my thanks. The «-naph- 
1) Journ. f. prakt. Chemie, 96, 254 (1917). 
8) The ethereal oil of tea was some time ago the subject of an investigation by 
Dr. Deuss (Mededeelingen van het Proefstation voor Thee, XLII, 21, 1917). This 
research merely confirmed our own observation that the oil contained an unsatu- 
rated alcohol together with methyl salicylate. 
