EEICACB^E 281
C. 85-2 per cent. H. 15'2 per cent.
Calculated for C^H^.
C. 85-3 ,, H. 14-7
The oil, separated as above-mentioned from the paraffin, was readily
soluble in 80 per cent, alcohol, and therefore could have contained no
hydrocarbon, and especially no sesquiterpene as stated by Trimble.
Any benzoic acid contained in the original oil would also have been
found in this liquid, as the esters of benzoic acid are very resistant
toward a cold solution of potash. Upon saponification of a small por-
tion with a hot alcoholic solution of potash a somewhat oily acid was
obtained, but no trace of benzoic acid could be detected.
The oil separated from the paraffin was then subjected to fractional
distillation, at first under ordinary pressure and finally in a vacuum.
The lower boiling portion formed a crystalline compound with sodium
bisulphite, and when isolated in this manner was found to have an
odour resembling cenanthol. By oxidation it yielded an acid having
the odour of the higher fatty acids. An analysis of its silver salt gave
figures corresponding approximately to the formula C 6 H 10 O 2.
After the separation of the body which yielded a compound with
sodium bisulphite, the oily liquid from the gaultheria was resolved by
fractional distillation into essentially two parts, the one distilling at
160° to 165° G. under ordinary pressure, the other at about 135° C.
under a pressure of 25 mm. or at 230° to 235° under ordinary pressure.
Both of these fractions possessed a highly penetrating and characteristic
odour, differing from each other, but which was so intense that a single
drop added to 5 c.c. of synthetic methyl salicylate almost completely
concealed the odour of the latter.
An analysis of the fraction boiling at 160° to 165° C. gave figures
agreeing with the formula C 8 H 16 0.
Calculated for C 8 H 16 O:— Found :—
- C. 75-0 per cent. 7*49 per cent. 74'9 per cent.
H. 12-5 „ 12-3 „ 12-4 „
By treatment of this body with benzoyl chloride and a dilute solution
of sodium hydrate a benzoic ester was obtained. An attempt to obtain
a phenylurethane by treating the substance with phenylisocyanate was
not successful. On the other hand, by the reaction with the latter,
diphenylurea (melting-point 235° C.) was obtained, due to the elimina-
tion of a molecule of water. This indicated that the body in question
is a secondary alcohol. The above-mentioned body which combines
with sodium bisulphite may thus perhaps be regarded as the correspond-
ing ketone of this alcohol, which could then be readily converted into
an acid of the composition C 6 H 10 O 2.
The purification of the fraction boiling between 230° and 235° C.
was attended with great difficulty, as by distillation a slight elimination
of water constantly took place, and the liquid acquired a yellow colour.
Several analyses were made of it, without obtaining perfectly constant
results. The body was, however, characterised as an ester, and in fact,
according to the odour developed after saponification, as the ester of the
previously mentioned alcohol C 8 H 1 4O. The acid obtained from it by
saponification was of an oily nature, and had a peculiar unpleasant
odour, similar to that obtained from the previously mentioned aldehyde
or ketone. The analysis of its silver salt, which is readily decomposed
with the loss of acid, also gave a corresponding result. It is therefore
- C. 75-0 per cent. 7*49 per cent. 74'9 per cent.