— 26 — 
J 
derivative could be obtained from the subsequent fractions, which, 
judging by their physical constants and the odour, consisted chiefly of 
terpenes. The constants of the two fractions distilled over sodium were 
as follows: i. boiling point 165° to 170^, specific gravity 0,8567, op- 
tical rotation — 2°3i'(5omm), and 2. boiling point 170° to 180°, 
specific gravity 0,8631, optical rotation — 1° 1 (100 mm). The oil 
passing over at 180^ to 210° served for the isolation of the benzoic 
ester. It was oxidised at ordinary temperature with a i to 2 per cent, 
solution of potassium permanganate, until the violet colour of the solu- 
tion, which was gradually added to the oil in small quantities, remained 
unchanged. In this manner we obtained a liquid which had a distinct 
odour like methyl ester of benzoic acid, and boiled at 190° to 200^, 
and which, being slightly lighter than water, would still contain conside- 
rable quantities of foreign admixtures. As in spite of this the saponi- 
fication number was comparatively high (101,1) it was obvious that 
the oil had a high ester - content. By repeated careful fractionating 
we endeavoured, but unfortunately without success, to separate from 
it a fraction with a still greater ester - content. In consequence of 
paucity of material we were then compelled to abandon further attempts 
to produce it in the pure state, and to content ourselves with having 
proved that as a matter of fact an ester of benzoic acid was present 
in the oil. The saponification yielded a pure white acid crystallising 
in leaflets, which had the melting point 121°, could readily be sub- 
limed, and showed all the properties of benzoic acid. When heated 
with methyl alcohol and concentrated sulphuric acid, it formed methyl 
ester of benzoic acid with its characteristic odour. We would still 
point out that the boiling point of the ester fraction in question very 
closely approaches that of methyl ester of benzoic acid (199°). By 
means of saponification we succeeded in identifying the compound, 
which was present along with the ester, as methyl heptyl ketone. 
The oil driven off with steam from the saponification liquor, possessed 
a refreshing rue-like odour. The boiling point was at 191° to 196°. 
The capacity of reacting with bisulphite liquor, and of forming a semi- 
carbazone with semicarbazide in acetic solution, showed that the body 
was a ketone, or an aldehyde respectively. The semicarbazone melted 
at 118^ to 119^, and when submitted to elementary analysis gave 
values corresponding to those of the semicarbazone of methyl heptyl 
ketone. 
1. o,i6o6g of the substance yielded 0,3530 g COg and 0,1448 g HgO. 
2. o,i5iog „ „ „ „ 0,3321 g „ „ 0,1401 g „ 
Calculated for CioHgiONg: Found: 
C 60,30 percent. 59,94 percent.; 59,98 percent. 
H 10,55 10,15 „ „ 10,31 „ 
