P - 79 



B.p. 193 to 194°, 63 to 65° (4 mm.), d 15 o 0,9442, « D — 5° 25', n D20O 1,45191, 



Mol.-Refr. C 10 H 18 O 2 r 48,78 calc. 48,88; 

 B.p. 193 to 194°, 71 to 73,5° (6 to 7 mm.), d 15 o 0,9431, « D — 5° 46', 



n D 2oo 1,45221. 



Combustion: 



1. 0,1795 g. subst: 0,4652 g. C0 2 , 0,1721 g. H 2 0. 



2. 0,1597 g. subst.: 0,41 14 g. C0 2 , 0,1531 g. H 2 0. 



3. 0,1642 g. subst: 0,4250 g. C0 2 , 0,1583 g. H 2 0. 



Found Calc. 



1. 2. 3. f. C 10 H 18 O 2 , f. C 10 H 18 O. 



C 70,68 70,26 70,58 p. c. 70,60 77,92 p. c. 



H 10,65 10,45 10,71 p. c. 10,65 11,69 p. c. 



The body is somewhat viscous and is also clearly differentiated from 

 linalool by its mouldy odour, which reminds somewhat of fenchyl alcohol 

 and of camphor. As its b.p. is only 3 to 4° lower than that of linalool, 

 it is impossible, in view of the very small extent to which it occurs in 

 the oil, to prepare it in the pure form by fractionation. It is however 

 possible to obtain it in this form, although at a considerable loss of 

 material, by repeatedly oxidising the fractions containing linalool of high 

 sp. gr. with 0,5 p. c. permanganate solution under ice-cooling, each time 

 driving off the unattacked oil with steam. It also appears to be possible 

 to accumulate the compound by treating the fractions in question with 

 glacial acetic-sulphuric acid at 40 to 50° for several hours. It was 

 ascertained at the time, from the formation of esters, that the body 

 Ci Hi 8 O 2 represents an alcohol. Its acetic ester, of which the odour 

 differs altogether from that of linalyl acetate, boils between 60 and 65° 

 (4 mm.), its benzoic ester between 157 and 160° (3 to 4 mm.). When 

 treated with other reagents, such as phenylisocyanate, diphenyl carbamic 

 chloride, phthalic anhydride, semicarbazide, and bromine, no solid derivatives 

 were obtained. As an oxidation-product, first with permanganate and sub- 

 sequently with bichromate and sulphuric acid, the body yielded acetone 

 (m. p. of the bromophenylhydrazone, 92 to 94°) and in addition to acetic 

 acid, an oily acid which was possibly identical with la?vulic acid. 



For purposes of comparison we have prepared the linalool oxide 

 according to Prileshaeff's method by oxidation of linalool with benzoyl 

 kjiydrogen peroxide and have obtained preparations possessing the following 

 constants, which agree with those of the natural product. 



diso 



a D 



flD2oo 



b. p. 



0,9450 

 0,9449 

 0,9443 

 0,9441 



— 4°6' 



— 4°51' 



— 4° 46' 

 -5° 41' 



1,45231 

 1,45403 



55 to 56° (3 mm.) 



The odour of the synthetic product is exactly like that of the oxide 

 isolated from linaloe oil and also resembles the latter in its other 



