84 BACON. 



Fractions 1 io 5 seem to consist of a mixture of terpenes wit}i linaloiil and 

 benzyl alcohol, with possibly a small amount of amyl or hexyl alcohol. A special 

 experiment made to separate the terpenes from the alcohols by means of the 

 Grignard method according to the equation 



CH3MgH-a„H,sOH -^CioHisOMgl+CH, 



demonstrated that linalool as well as the alcohols of ylang-ylang oil give addition 

 products which are soluble in ether, so that no separation was possible. 



Fractioiis 6 and 7. — These fractions possess an odor much like that of linalool 

 and in addition another, sweet one, is present. Oxidation of 9 grams of the 

 united fraction with dilute potassium permanganate gave 1.2 grams of benzoic 

 acid melting at 121°. This corresponds to 13.3 per cent of benzyl alcohol. 



A small portion of these fractions was oxidized with potassium bichromate and 

 dilute sulphuric acid, and by this means the odors of benzaldehyde and of citral 

 were obtained. 



The fractions 6 and 7 were also heated with finely powdered calcium chloride 

 for one hour on a steam bath and then kept in a cool place for twenty-four liours. 

 A solid compound with calcium chloride separated, this was filtered with the aid 

 of a pump, and well washed with ether. Twenty-nine grams of an oil boiling 

 between 200° and 206° at ordinary pressure were obtained on decomposing this 

 addition product with water. This body had the odor of benzyl alcohol and 

 proved to be the latter almost in its entirety by conversion into benzyl acetate, and 

 also by obtaining an 85 per cent yield of benzoic acid by oxidation. The liquid 

 not entering into combination with calcium chloride, proved itself to be almost pure 



30° 

 linalool, as is sliown by the following constants: Specific gravity, --^=0.8586; 



30° 30° 



A = — 16°; N--- = 1.4655; boiling point 190° to 195° at ordinary pressure. 



The odor of this portion was identical with that of linaloiil, and citral was 

 produced from it by oxidation with potassium bichromate. 



Fraction S. — This portion was separated into 10 grams of benzyl alcohol, 11 

 grams of linalool, and 3 grams of an oil which solidified with calciiun chloride, 

 boiled at a higher point than benzj'l alcohol and therefore from its odor and the 

 formation of an addition product with calcium chloride it was determined to be 

 geraniol. 



Fraction 9. — This fraction, on treatment with powdered calcium chloride im- 

 mediately became hot and solid. This method of separation gave 8 grams of an 

 oil not acted upon by calcium chloride and having a refractive index of 



30° 

 N = 1.5131. This portion had the odor of safrol. Oxidization with acid potas- 

 sium bichromate gave the odor of heliotrope. Tlie oil which was separated from 

 llie calcium chloride compound possessed a pronounced geraniol odor, boiled at 



108° to 115° at 10 millimeters; specific gravity -^=0.881; K^ = 1.4821. 



Fraction. K) was similarly separated into 12 grams of geraniol, a small amount 

 of safrol, and into sesquiterpenes. 



Fracliona 11 and 12 consisted almost entirely of sesquiterpenes, among which 

 cadinene is present, as a small yiehl of eadiucuc hydrochloride melting at 117° 

 was obtained on treating 10 grams of this fracliun. dissohcd in ether, witli dry 

 hTdrogen chloride. 



