142 Report of Schimmel $ Co. April 1913. 



methylheptenone is explainable only by the presence of tetrahydroxylene (IV) in the 

 hydrocarbon mixture. 



Wallach surmises that in the course of the auto-condensation of methylheptenone 

 dihydroxylene is primarily formed, and that a portion of this body gives off two hydrogen- 

 atoms, under formation of xylene, while another portion absorbs two atoms of hydrogen, 

 giving rise to tetrahydroxylene. 



COCH3 



CCH 3 



H 2 c/\CH 



CCH 3 



HCCH 3 



H 2 C ( / \CH 2 



H,cl Jc-CH, 



CH 



> 



H 2 C\ JCCH ;! 



CH 



Hcl Jc-CH, 

 CH 



H 2 Cl JCCH 3 

 CH 



(I) Methylheptenone. 



(II) ^i^-Dihydro-Hi-xylene. 



(III) ^-Xylene. 



(IV) Tetrahydro-wi-xylene. 



Pinone, demethylated. In the course of the dry distillation of the calcium 

 salt of cis-hexahydro «'sophthalic acid, O.Stark 1 ) has obtained a ketone which he is 

 inclined to consider as a demethylated pinone, of the formula given below. It boils 

 between 157 and 158° (758 mm.) and possesses an extremely pronounced, characteristic, 

 somewhat camphoraceous odour. d 20 o 0,9322, n D20 o 1,4731. Its semicarbazone melts 

 between 179 and 180°. 



CH 



H * c rioi CHs 



H>Cl \>CH 



CHa 



Demethylated pinone. 



Cyclic ketones. In our Report of October 1912 (p. 155) we referred to a paper 

 by Wallach on the condensation-products of cyclic ketones with acetone, which had 

 appeared in the Nachrichten der Koniglichen Gesellschaft der Wiss. zu Gottingen, meeting 

 of February 17. tn . Detailed particulars of Wallach's investigations have now been 

 published in another quarter' 2 ). 



Menthone. J. Waning, while treating magnesium methyliodide with menthone, 

 obtained methyl-3-menthanol-3: b. p. 102 to 103° (16 mm.), d~ 0,9143. The chloride 

 boils at 101 to 103° (13 mm.); and when heated with sodium bisulphate yields the 

 hydrocarbon CuH 20 , b. p. 185 to 187°, df ° 0,8244. 



Camphor. A few physical constants of camphor are quoted on p. 131. 



Thujone. On p. 166 of our last Report we pointed out that pure thujane may 

 be prepared from thujylidene hydrazine. Kishner 4 ), while treating such a preparation 

 with fuming hydrobromic acid, obtained bromides of which the stability depended on 

 the duration of the reaction. After the elimination of hydrobromic acid the bromides 

 afforded several hydrocarbons. 



*) Berl. Berichte 45 (1912), 2369. — 2 ) Liebigs Annalen 394 (1912), 362. — 3 ) Journ. russ. phys. chem. 

 Ges. 44 (1912), 1068; Chem. Zentralbl. 1913, I. 24. — 4 ) Journ. russ. phys. chem. Ges. 44 (1912), 1759; Chem. 

 Zentralbl. 1913, I. 706. ... 



