228 ODOROGRAPHIA. 
into benzoyl-eugenol, C,;H,,O3, by first agitating with caustic 
potash or soda solution, and then adding an equivalent of benzoyl 
chloride, C;H;OCl. Upon shaking, a considerable heating of the 
mass takes place, which is sufficient to complete the formation of 
the benzoyl-eugenol which is found in a crystalline mass on cooling. 
In order to remove a small quantity of sesquiterpene adherent, the 
crystalline mass, after beg washed several times, is heated on a 
water-bath in a definite quantity of 90 per cent. by weight of al- 
cohol (25 c. ec. where 5 grammes of the oil has been taken). The 
mixture is stirred until complete solution takes place, then cooled 
to 17° C. and filtered, sufficient alcohol being added to make up 
for any loss. The filtrate at this temperature contains all the 
sesquiterpene, together with a small quantity of benzoyl-eugenol, 
amounting to 25 c.c. to 0°55 gramme. The crystalline mass is 
then placed, with the still moist filter, im a weighing-bottle, the 
weight of which, together with that of the filter, dried at 101° C., 
has previously been taken, and dried at 101° C. until of constant 
weight. From the weight of this benzoyl-eugenol, after an addition 
has been made for the quantity remaining dissolved in the filtrate, 
the quantity of eugenol present in the oil taken can be calculated 
in the usual way; the molecular weight of the former compound 
being 164 and the latter 268. 
Experiments made by Messrs. Schimmel to test the accuracy of 
this process resulted as follows :— 
1, Eugenol prepared by saponification of benzoyl-eugenol, sp. 
gr. 1:072 at 15° C. Boiling-point 253°-254° C. Forms a clear 
solution in 1-per-cent. caustic-potash solution. 5 grams yielded 
8°22 gram benzoyl-eugenol, equivalent to 100°6 per cent. eugenol. 
Hs 8:22 x 100 x 164 
5 x 268 = 100°60. 
2. Eugenol obtained from clove-oil by shaking with alkali. Sp. 
gr. and boiling-pomt exactly the same as No. 1. 5 grams yielded 
8°20 grams benzoyl-eugenol, equivalent to 100°35 per cent. eu- 
genol : 
8°20 x 100 x 164 
ae SS OOO 5: 
5 x 268 002 
3. Eugenol prepared as No. 2, but a less pure product. Formed 
a clear solution with 10-per-cent. caustic-potash solution, but turbid. 
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