— 128 — 



ing constants: b. p. 124 at 11 mm. press., d £5 0,9133, d^ 0,8954, 

 n D25° i»49468, [«]d25° — 66,11°, mol. refr. determined 66,46, calculated 

 for a bi- cyclic hydrocarbon C 15 H 24 / = 66,2 8. The whole of these 

 results show that guajol is a tertiary sesquiterpene alcohol with one 

 ethylene linking. 



Aldehydes. 



In the action of organic acids or acid anhydrides upon aldehydes, the 

 formation of di- esters or unsaturated acids is a well-known phenomenon. 

 F. W. Semmler 1 ) has now further been able to prove that aldehydes 

 in which a labile hydrogen atom is found in an adjoining position 

 the CHO-group, are more or less easily able to yield mono-esters 

 when subjected to the treatment mentioned above, in which process 

 a conversion of the aldehyde into the enolic form (i. e. into the vinylic 

 form) is to be assumed. Thus, santalol, when oxidised with ozone, 

 yielded saturated tricyclic eksantalal 2 ), C n H 16 O, which was now, after 

 being purified by means of the bisulphite combination, found to possess 

 the following constants: b. p. 112 to 113° at 10 mm. press., d2o° 0,987, 

 n D 1,4881, «p about -j- 12°. This eksantalal, when boiled for an 

 hour with acetic anhydride yielded, in addition to a slight quantity 

 of diacetate, about 8o°/ of enol- eksantalal mono-acetate (dihydro- 

 eksantalol acetate), C 10 H 14 : CH • O • CO • CH 3 . This combination pos- 

 sessed the following properties: b. p. 132 to 13 5 at 10 mm. press., 

 d2o° 1,023, n D 1,4881, «p — 7 15'. By heating with water or dilute 

 mineral acids at no° under pressure, this body could be split up 

 again into the aldehyde. Reduction with sodium in alcoholic solution 

 produced eksantalol C 11 H 18 0. Whereas even with ozone no carbon 

 atom split off from eksantalal, which indicates the saturated character 

 of the body, the ester yielded a tri-cyclic ketone: nor-eksantalone, 

 C 10 H 14 O, with the following constants: b. p. 101 to 102° at 10 mm. 

 press., d2o° 0,988, n D 1,485, molec. refr. found 43,51, calculated 42,92. 

 Its oxime boiled at 142 to 144° under 10 mm. pressure, and its 

 semicarbazone melted at 21 6°. The corresponding alcohol, nor-ek- 

 santalol, C 10 H 16 O, boiled (10 mm. pressure) at 116 to 11 8°. 



Phenylacetaldehyde, which behaved entirely analogously, was 

 found to possess the following constants: b. p. 85 to 86° und 10 mm. 

 press., d2o° 1,0252, n D 1,53191, molec. refr. found 36,9, calculated 

 for C 8 H 8 0/4^36,7. Upon boiling with acetic anhydride it yielded 

 about 8o°/ of enol -phenylacetaldehyde mono -acetate (phenylvinyl 

 acetate, dihydro phenyl ethyl acetate), C 6 H 5 -CH:CH«0-CO« CH 3 : 

 b. p. 119 to 121° at 10 mm. press., d2o° 1,065, n J> l >54%3> molec. 

 refr. found 48,2 1, calculated for C 10 H 10 2 /i~46,32. Reduction produced 



x ) Berl. Berichte 42 (1909), 584. 



2 ) Compare Report October 1907, 85; November 1908, 182. 



