





— 



127 — 













Santalol Santalene 



Santalene 



Santalene 





(Schimmel $ Co.) (Schimmel $ Co.) 



(Semmler) 



(Guerbet) 





a 



fi a 



P 



a 



fl 



a 



fi 



B.p. 



148° (4,5 mm) 



158 to 158,5° 



118° (7 mm) 



125 to 126° 



118 to 120° 



125 to 127° 



252 to 



261 to 262° 







(5 mm) 



252° (753mm) 



(7 mm) 



(9 mm) 



(9 mm) 



252,5° 





d 



0,9788 (15°) 



0,9728(15°) 



0,9132(15°) 



0,8940 (20°) 



0,8984(20°) 



0,892(20°) 



0,9134(16°) 



0,9139 (00) 



a 



4-1013' 



— 41° 47' 



— 3°34 f 



— 41°3' 



— 15° 



— 35° 



— 13,98° 



- 28,55° 



"d 



1,49915(20°) 



1,50910(20°) 



1,49205(15°) 



1,49460(200) 



1,491 



1,4932 







Mol. 



















refr. 



66,23 



calc. f. 



C15H24O/F 



65,93 



67,77 



calc. f. 



C15H24O/J 



67,64 



64,87 

 calc. f. 



Cl5H24/f 



64,45 



66,53 



calc. f. 



C15 H24 /2 



66,16 



65,8 



66,55 







Guerbet 1 ) had employed the nitrosochlorides for the purpose of iden- 

 tifying the santalenes. In this case Wallach's method of preparing nitro- 

 sochlorides is unsuitable, as had already been observed by v. Soden and 

 Miiller 2 ), but we have obtained favourable results by following the method 

 of Ehestadt 3 ). The nitrosochloride obtained from the first fractions melted 

 at 112 to 117°. 



We were also interested in making the acquaintance of another pro- 

 duct which had already been prepared from santalene by v. Soden and Miiller. 

 By hydration according to Bertram und Walbaum's method as modified 

 by Wallach for caryophyllene, v. Soden and Miiller obtained an inactive 

 alcohol. Guerbet repeated their experiments, but without result. On the 

 other hand, he prepared the acetates by heating the santalenes with glacial 

 acetic acid under pressure at 180 to 190°. We hydrated fractions which 

 the molecular refraction indicated as consisting chiefly of tricyclical 

 ^-santalene, and obtained about 5 to 10°/o of an alcohol with a cedarwood- 

 like odour. B.p. 154 to 157° (5 to 6 mm.); d 15 o 0,9787; d 20 o 0,9753; n D20O 

 1,51725; mol. refr. found 68,81; calc. for Ci 5 H 26 /T 68,07. 

 0,1213 g. subst.: 0,3606 g C0 2 , 0,1250 g H 2 0. 





Found 



Calculated for 

 Ci 5 H 24 Ci 5 H 26 



c 



81,09°/o 



81,81 °/o 81,08°/o 



H 



ll,45°/o 



10,90°/o ll,71°/o 



With concentrated formic acid this alcohol readily gave off water, 

 even at so low a temperature as that of the human hand. It was not 

 oxidisable with chromic acid, and is therefore probably a tertiary alcohol. 



J ) Bull. Soc. chim. III. 23(1900), 540 and 542; Compt. rend. 130(1900), 1324; Report October 

 1900, 58. 



2 ) Pharm. Ztg. 44 (1899), 259. 

 *) Report April 1910, 164. 



