- 3 5 - 



with a lower content of hydrogen. Shortly afterwards v. So den 1 ) 

 also found for a-santalol, which represents by far the larger portion 

 of santalol, the formula C 15 H 24 0. This result is now confirmed by 

 a new work by Semmler and Bode 2 ) which for the rest deals with 

 the question of the constitution of santalol. 



According to this work, the authors were successful in converting 

 santalol by oxidation with chromic acid in solution of glacial acetic 

 acid, into the aldehyde santalal, which, regenerated from the semi- 

 carbazone (m. p. about 230 ) possesses the following properties: b. p. 152 

 to 155 (10 mm. pressure); d 20 ° 0,995; «p + J 3 t0 + *4°; n n 1^51066; 

 molecular refraction found 65,6, calculated for C 15 H 22 0/~ 64,63. 

 Crude santalal contained, besides admixtures of an alcoholic character, 

 probably a lsevorotatory santalal of the same formula C i6 H 22 0. As 

 santalal could be converted into an oxime (m. p. 104 to 105 ), this 

 into a nitrile, and the latter by saponification into an acid C 15 H 22 2 , 

 santalic acid (b. p. 192 to 195 at 9 mm. pressure), the aldehydic 

 character of santalal is proved, which confirms the present assumption 

 that santalol is a primary alcohol. The further oxidation of santalal 

 with potassium permanganate or ozone, yielded the same tricyclo 

 ecsantalic acid C u H 16 2 as santalol itself (see below). By treatment 

 with phosphorus pentachloride, a chloride was obtained from santalol, 

 which on reduction with sodium and alcohol yielded a sesquiterpene 

 C 15 H 24 (y-santalene, b. p. 118 to 120 at 9 to 10 mm. pressure; 

 d2o° °>9355)- When submitted to the action of sodium and alcohol, 

 santalol did not change, but reduction with phosphorus and hydriodic 

 acid in a sealed tube at 180 yielded a not entirely uniform hydro- 

 carbon. Hydrocarbons were also formed when santalol was heated 

 in a sealed tube to 310 . 



The oxidation of santalol with potassium permanganate yielded in ad- 

 dition to dihydroxy-dihydro santalol C 15 H 26 3 , tricyclo ecsant- 

 alic acid C u H 16 2 (b. p. 165 to 167 at 10 mm. pressure; m. p. after 

 crystallisation from water or glacial acetic acid 71 to 7 2°), which 

 supplied an insoluble copper and silver salt. From the methyl ester 

 of this acid there was obtained by reduction with sodium and alcohol, 

 the lsevorotatory alcohol tricyclo ecsantalol C u H 18 (b. p. 130 to 

 132 at 10 mm. pressure; d2oo 0,9859; n D 1,49478; molecular refraction 

 found 49,1, calculated for C 11 H 18 47,45, for C 11 H 18 0/"49,66), 

 which could be oxidised with chromic acid in solution of glacial acetic 

 acid into the aldehyde tricyclo ecsantalal C^H^O (b. p. 125 to 

 130 at 13 mm. pressure; d2o° 1,012). When oxidising santalol with 

 ozone, the same tricyclo ecsantalic acid was formed as in the oxidation 



4 ) Arch, der Pharm. 238 (1*900), 353; Report October 1900, 59. 

 2 ) Berl. Berichte 40 (1907), 11 24. 



