( 105 ) 
The above does not altogether apply to the action of acetic anhy¬ 
dride on linalool, which has been studied successively by Barbier l 2 ), 
Stephan *) and Zeitschel *). The last investigator has obtained a 
hydrocarbon, whose sp. gr. (e? 15 = 0.813) was considerably lower 
than that of dipentene and terpinene and comes near to that of the 
aliphatic terpenes; Zeitschel speaks of “ein olefinisches, dem Myrcen 
sehr nahe stehendes Terpen” 4 ). It appeared to me desirable to 
attempt the dehydration of linalool with a neutral or alkaline 
substance. 
Sabatier and Senderens have found in active copper (prepared by 
reducing copper oxide at 200°) a contact substance, which accelerates 
addition of hydrogen in a less degree than active nickel, but which 
can split up tertiary alcohols into water and hydrocarbons. A specimen 
of linalool of high optical rotation (/<£> = —17°14'), kindly presented 
to me by Dr. Gildemeister, chief-chemist to Schimmel and Co., was 
passed at 135° over active copper and fully one-half was split up 
into hydrocarbon and water. By fractionating the product of the 
reaction, finally over metallic sodium, the main product, an optically 
active hydrocarbon of the formula C 10 H 1# is obtained. The constants 
of the fractions are: 
| Fraction B.p. 12 d 16 «/>(100mM) nd lx H y — H« 
I 66° — 68° 0,8401 
II 67.5°—68.5° 0,8344 
III 68.5°—69° 0,8339 
IV 69° — 70 3 0,8340 
(mol. disp.) 
1,4802 1.84 
(MR = 46,1) 
The boiling point of the first fraction at the ordinary pressure is 
171°—173°. The odour of the three last fractions reminds one of 
that of limolene, that of the first one of myrcene. This fraction also 
differs in the constants whereas the other fractions agree. Assuming 
that, in the main, a single substance is obtained, which according 
to the constants cannot be limonene or terpinene (these terpenes 
have a 8° higher b. p.), I have more closely investigated the tractions 
II—IV and now give a preliminary communication of the results of 
the investigation. 
The molecular refraction and dispersion are very peculiar. Of the 
J ) Gompt. rend. 116, 1200 (1893). 
2 ) J. pr. Ch. [2], 58, 109 11898). 
8 ) Ber. 39, 1780 (1906y 
4 ) Compare: Stephan, pr. Gh. [2] 58, 113 (1899) and Semmler, Aetherische Oele, 
Bnd I, 549 (1906). 
8 
Proceedings Royal Acad. Amsterdam. Vol. XII. 
