— 125 — 



out the oxidising process in acetone solution with strong cooling, 

 caryophyllene yielded a compound C 10 H 18 O 3 , melting at 146 , which 

 was judged by its behaviour to be a glycol. 



Alcohols, 



A. Windaus 1 ), in a paper on rendering saponin non-toxic by 

 means of cholesterol, states that digitonin may be combined with 

 linalool, geraniol and sabinol into a crystalline compound. 



Linalool. By reducing linalool by means of nickel and hydrogen, 

 C.J. Enklaar (as already mentioned in our last Report) 2 ) obtained 2, 

 6-dimethyl octane. We gather from a new paper by Enklaar 3 ) that in ad- 

 dition to this hydrocarbon he obtained 2, 6-dimethyl octanol-6 (C H 3 ) 2 • C H 

 .(CH 2 ) 3 .C(OH)(CH 3 ).CH 2 .CH 3 (b. p. 88 to 88,5° at 14mm. press.; 

 d— 0,836; n Di5o 1,4388) which points to the accuracy of Tiemann's 

 and Semmler's formula for linalool, viz., (CH 3 ) 2 :C : CH«CH 2 -CH 2 

 • C (O H) (C H 3 ) • C H : C H 2 . By the reaction of magnesium ethyl iodide 

 on 2-methyl heptene-2-one-6 there was formed 2, 6-dimethyl octene- 

 2-0I-6 (CH 3 ) 2 .C:CH.CH 2 .CH 2 .C(OH)(CH 3 ).CH 2 .CH 3 (b. p. 94 

 to 94,5° at 14 mm. press.; d^- 0,8695; n D15Q 1,4569) which, when 

 reduced with nickel and hydrogen also yielded 2, 6-dimethyl octane 

 and 2, 6-dimethyl octanol-6. 



Menthol. In a preliminary communication, R. H. Pickard and 

 W. O. Littlebury 4 ) refer to experiments for the separation of stereo- 

 isomeric menthols by the aid of their acid phthalic, or succinic esters. 

 Thymomenthol, a body of a low melting-point, obtained by the reduction 

 of thymol by Sabatier's process, had already been converted by 

 Brunei 5 ) by esterification and subsequent hydrolysis into an isomeride, 

 a-thymomenthol, The latter contains three, if not all four of the 

 theoretically possible racemic combinations. Two of these can be 

 characterised accurately and split up into their active component parts. 

 One of these racemic menthols melted at 25 , the acid succinic ester 

 at 86°, and the acid phthalic ester at 13 1°. From the fractionated 

 crystallisation of the cinchonine or brucine salts of the last-named, a 

 laevorotatory isomeride was obtained which, upon saponification, yielded 

 a menthol with the same melting-point and rotation as the natural 



*) Berl. Berichte 42 (1909), 244. 



2 ) Report November 1908, 153. 



3 ) Recueil des trav. chim. des P.-B. 27 (1908), 411. Through Chem. Zentralbl. 

 1908, II. 1926. 



4 ) Proceed, chem. Soc. 24 (1908), 217. 



5 ) Compt. rend. 140 (1905), 252; 141 (1905), 1245; Report April 1906, 117. 



