— 119 — 



The ketone was liberated by boiling with dilute sulphuric acid. Under 

 distillation by steam it already began to deposit itself in the solid form 

 in the condensing tube, and it therefore became necessary to remove 

 it with ether from the mother-liquor. When purified by fractionation the 

 ketone, which had an odour of camphor and cineol, boiled at 193 to 195° 

 and melted at 48 to 52° ([«] D — 4°40' in a 18,9°/o alcoholic solution). 

 An attempt was made, but without much success, to recrystallise the 

 ketone from light petroleum with a low b. p. The m. p. was then found 

 to be 58 to 61°. 



Combustion showed that the compound has the formula C 9 Hi 4 0. 

 The readiness with which it condensed with semicarbazide indicated the 

 presence of a carbonyl-group; while its completely neutral behaviour 

 towards magenta solution decolorised by sulphurous acid, ammoniacal 

 silver solution, and permanganate made it highly probable that the body 

 was a saturated ketone. 



Boiling with excess of hydroxylamine produced a liquid oxime with 

 a b. p. of 110 to 113° (6 mm.). The ketone could not be regenerated by 

 heating with acids, but in the place thereof a nitrile odour became per- 

 ceptible. When condensed with benzaldehyde an oily benzylidene-com- 

 pound was obtained. 



These properties of the ketone pointed to its identity with ^-nor- 

 camphor, which was obtained by Semmler 1 ) from teresantalic acid, or 

 with santenone, which was prepared by Aschan 2 ) from santene. In order 

 to obtain conclusive evidence on this point it was necessary to compare 

 the new sandalwood oil ketone direct with the santenone. With this 

 object in view we hydrated santene according to the Bertram-Walbaum 

 method, thereby obtaining an ester with an odour reminding of bornyl 

 acetate and possessing the following proporties: b. p. 79 to 81° (5 mm), 

 d 15 o 0,9971, « D ±0, n D20O 1,50121. 



The alcohol obtained by saponification, which was called santenol 

 by Aschan, boiled between 194 and 196° and had a melting-point of 82 

 to 84°, which was further increased to a small extent after recrystalli- 

 sation from low boiling light petroleum. Aschan used the phenylurethane 

 for identifying this alcohol. He states that santenol and phenyl isocyanate 

 form a vitreous mass from which, in addition to liquid products, a phenyl- 

 urethane melting at 61 to 62° is obtained. When, in the course of preparing the 

 urethane, the reaction mixture is left alone for some time, a solid crystalline 

 mass results, from which the urethane can be recovered by the familiar 

 process. Recrystallised from light petroleum, this urethane melts at 79 to 

 80°; with dilute alcohol it gives small, fine needles, melting at 83°. 



When oxidised with Beckmann's chromic acid mixture, santenol 

 yielded a small quantity of santenone (m. p. 42 to 47°; b. p. 193 to 194°), 



x ) Berl. Berichte 40 (1907), 4465; 41 (1908), 125; Report April 1908, 93. 

 -) Berl. Berichte 40 (1907), 4918; Report April 1908, 84. 



