— 169 — 



in alcoholic solution with nitric acid (d 1,255), an ample yield of 

 terpine hydrat, m. p. 116 to 117 , is obtained. 



CH C H 2 CH 2 C H 2 



/NT" \ / \ / CHs 



CH,= ( /C^ )CH -> CH 3 — COH CH — COH 



Xch, csy \ / \ CHg 



C H 2 C H 2 C H 2 C H 2 



/?-Pinene Terpin-hydrate 



Wallach had already on a previous occasion, while oxidising /?-pinene, 

 obtained pinene-glycol x ), m. p. 75 to 77 . If this glycol really possesses 

 the constitution attributed to it, it ought to be converted into nopinic 

 acid upon oxidation. As a matter of fact this acid (m. p. 126 to 127 ) 

 was obtained by carrying out the process of oxidation by means of 

 1 per cent, solution of permanganate with the addition of a few drops 

 of caustic soda liquor, at o°. If on the other hand the glycol be oxid- 

 ised at 50 , no nopinic acid, but another acid which has not been 

 more closely investigated, is obtained. 



Isopinene, Pinolene. In an earlier Report we stated that 

 Aschan 2 ) by decomposing the mixture of liquid chlorides eliminated 

 in the process of preparing pin en e hydrochloride with bases, had iso- 

 lated a hydrocarbon which he called pinolene. From pinolene hydro- 

 chloride he obtained by treatment with aniline an isomeric terpene to 

 which he gave the name of isopinene. In a new article, which deals 

 with both terpenes, Aschan 3 ) publishes the constitution of isopinene, 

 which he has ascertained with some certainty. He further discovered 

 pinolene to be a mixture of two hydrocarbons which he calls a- and 

 /?-pinolene. By oxidising by means of permanganate of potassium 

 at 60 to 8o° the two were separated, the a-pinolene being completely 

 destroyed, while f$ -pinolene was not attacked. When quite pure, 

 /?-pinolene appears as a liquid possessing the following constants: b. p. 

 142 to 144 , d'^ 0,8588, « D -(- 0,24°, [«] D -f- 0,28°, n D2 o° 1,44769, 

 mol. refr. found 42,37, calc. 41,83 for a tri-cyclic saturated hydrocarbon, 

 or 43 j 53 f° r a hydrocarbon with one ethylene-bond. 



From /?-pinolene Aschan obtained, without recrystallisation, a hydro- 

 chloride melting at 25 to 2 6° which does not appear to be identical 

 with that previously prepared from pinolene 4 ), although, when treated 

 with anilin it also yields isopinene. The acid (m. p. 200 ) which has 

 previously been detected when oxidising pinolene with permanganate 



x ) Liebigs Annalen 363 (1908), 1; Report November 1908, 172. 



2 ) Berl. Berichte 40 (1907), 2250; Report October 1907, 136. 



3 ) Ofversigt af Finska Vetenskaps-Societetens Forhandlingar 51, 1. Afd. A, 

 Nr. 9. From a copy kindly sent to us. 



4 ) Report October 1907, 136. 



