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The first fraction, boiling from 228° to 240°, amounted to about 
5 grams, and had an extremely disagreeable odour, which, however, did not 
remind of patchouli. In view of the small quantity available, nothing 
could be decided as to the character of the unpleasantly smelling body. 
We were equally unsuccessful in our endeavours to identify a body 
in the portions passing over between 240° and 260°. We therefore 
continued our examination with larger quantities of material. On the 
strength of preliminary trials in which we extracted patchouli oil with 
alcohol of varying percentage, we extracted 22 kilos oil with 70 per cent, 
alcohol, and thereby obtained an enrichment (though only slight) of 
the more readily soluble, smelling constituents. 
The alcohol was removed from the oil dissolved in vacuo. The 
latter did not differ in any marked degree in the physical constants 
from the original oil, but we were now able to detect some bodies. 
The quantity of oil, amounting to 7,2 kilos, was fractionated in vacuo. 
Benzaldehyde. Traces of this body were present in the lowest- 
boiling portions (54° to 70^ and 70° to 95°, at 4 mm pressure). It was 
detected by the semicarbazone of the melting point 214*^, from which 
dilute sulphuric acid during boiling liberated the characteristically smelling 
aldehyde. The melting point of the above-mentioned derivative was 
not lowered by adding the semicarbazone from the synthetic aldehyde. 
Eugenol. By repeated treatment with dilute soda liquor, we ab- 
stracted from the oils passing over between 70^ and 108"^ and 108° 
to 125^ (4 mm pressure), a phenol which after distillation in vacuo was 
recognised already by its odour as eugenol. The bulk (8 gm.) boiled at 
109° to 110°, at 5 mm pressure, and 253° to 256° at ordinary pressure; 
djgo = 1,0705. The benzoyl compound obtained according to 
Schotten-Baumann melted at 69° to 70°. The phenol in alcoholic 
solution showed with ferric chloride the well-known eugenol colouration. 
Traces of a slightly lower boiling phenol appeared to be mixed with 
the eugenol. 
Cinnamic aldehyde. On shaking the above fractions with bi- 
sulphite liquor, traces of a bisulphite compound separated off. The 
aldehyde regenerated from the latter had a distinct odour like cinnamic 
aldehyde. Its semicarbazone was characterised by difficult solubility 
in alcohol, and, like the synthetic semicarbazone, melted at 208°. The 
mixture of the two had the same melting point. 
Terpenic Alcohol. From the portions distilling under diminished 
pressure at 54° to 95°, we isolated, by heating the oil in benzene solution 
with phthalic acid anhydride for about one hour on the water bath, a few 
drops of an alcohol which had a very pleasant rose-like odour. An 
attempt to produce a solid derivative of it — in this case a diphenyl 
urethane, — failed. Possibly it is here a question of a higher alcohol 
of the aliphatic series. 
