( 725 ) 



which is formed from myrcene in the manner indicated ; tlieir state- 

 ments, liowever, are often diametrically opposed. 



Power and K],eber'), who first prepared it, took it to be linaloöl 

 on account of its odour and the formation of citral on oxidation 

 with chromic acid. Barbier'') declared it to be a new alcohol; on 

 oxidation, he obtained no citral but another as yet unknown aldehyde. 

 From the results of the oxidations he deduced for this alcohol, which 

 he named myrcenol, a structural formula, which had been given 

 already by Tiemann and Semmler to linaloöl. Tn a further research 

 on linaloöl, he gave as his opinion ') that it was not a simple 

 alcohol, but a mixture, and also that its main constituent was not 

 optically active, a reason why he rejected the formula of T. and S. 

 Semmler''), however, looked upon myrcenol as a mixture already 

 partly converted into cyclic products, and upheld his linaloöl formula 

 against Barbier's objections. 



I prepared the myrcenol according to the directions of Power and 

 Kleber. The greater part of the myrcene was recovered unaltered 

 (67o). a small portion polymerised whilst the alcohol had formed to 

 the amount of about 20°/„. For this alcohol distinguished from linaloiU 

 also by its intense, agreeable odour, I obtained the constants attributed 

 to it by Barbier, who, however, had a much langer quantity of the 

 alcohol at his disposal : 



sp. gr.,5 ml,, Bp. at 10 mM. Mol. Refr. 



myrcenol (^): 0,9032 1.4806 97—99° 48,44 



(B): 0,9012 1.47787 99° 48,34 



MR, calculated for C,„H,, 01== 48,16 



My analyses also pointed to the composition Cm Hjj, 0. I do not 

 consider this alcohol to be perfectly pure as it has not got a quite 

 constant boiling point ; it seems still to contain a more volatile fraction. 



Tiie closer investigation of this substance has, as stated, led to 

 dilferences of opinion. It seems to me that these have been caused 

 by the ditferent methods used. The formation of citral in the oxidation 

 in acid solution is no reliable test for the presence of linaloöl as it 

 may be yielded also by other alcohols. Barbier showed, however, that 

 on oxidation of myrcenol with chromic acid an aldehyde was formed, 

 having the same formula as citral, but not identical with the same. 

 He regenerated it, for instance, from its oxime, and obtained a 



1) 1. c. 



2) Bull. Soc. Ghem. [3], 25, 687 (1901). 



3) Bull. Soc. Ghem. [3]. 25, 828 (1901). 

 *) Ber. 34, 3122 (1901). 



