— 5i — 



with a i per cent, permanganate solution. The hydrocarbon which 

 hat not been attacked consisted almost entirely of p-cymene. The 

 oxidation liquors were evaporated and extracted with chloroform. The 

 glycol which was isolated was a viscous oil which could not be 

 brought to congealing. With dilute sulphuric acid we obtained a body 

 of a pronounced odour of cumin, of which the semicarbazone melted 

 at 205 to 208 °. The parts which were not attacked by the semi- 

 carbazide probably represented a hydrated cuminic alcohol, which 

 was converted by oxidising with chromic acid into cuminic acid, 

 m. p. 113 to 1 1 5°. The aldehyde which was reconstituted from the 

 semicarbazone was also converted into the same acid. Hence, these 

 fractions must contain a hydrocarbon with a methene-group connected 

 to the nucleus, for only such a body is able to form, when oxidised, 

 a glycol which when water is eliminated therefrom is converted into an 

 aldehyde and an alcohol of the cumin series. In addition to this 

 glycol there was formed a mixture of oily acids from which, 

 however, only ^butyric acid could be isolated. The b. p. of this 

 was 157 to 1 59 ; its calcium salt dissolved more readily in cold 

 than in hot water. From what particular hydrocarbon these oxidation 

 products were derived could not be exactly determined, but it may 

 be safely assumed that they indicate the presence of /?-phellandrene; 

 for /?-terpinene, which would yield similar products, could not be 

 detected by other methods. 



In order to settle also the question as to what particular hydro- 

 carbons are the source of the liquid chlorides which are formed in 

 ample quantities in the course of the preparation of the chlorides, 

 these liquid chlorides were subjected to closer examination. The bulk 

 of them boiled between 83 and 85 (5 mm.). 



0,1554 g. gave 0,1901 g. AgCl, corresponding to a content of 

 30,240/0 CI. Calculated for C 10 H 18 C1 2 , 33,97% CI; for C 10 H 17 C1, 

 20,58 °/ . The values agree to some extent for dihydrochlorides. 



22 g. of the liquid dihydrochlorides were shaken up for 4 hours 

 at 50 with 25 g. potassium hydroxide and 1250 ccm. water and this 

 operation was repeated until the oil ceased to give a chlorine reaction. 

 The volatile constituents were then driven off by steam distillation. 

 In the residue only cis-terpin hydrate, m. p. 117 to 11 8°, could be 

 detected. The portions which volatilised with steam contained dipentene 

 (tetrabromide, m. p. 123 to 125 ) and a-terpineol, m. p. 33 to 34 . 

 The alcohol which had not solidified, when treated with hydrochloric 

 acid, yielded dipentene dihydrochloride, m. p. 48 to 49 , and when 

 oxidised, a glycerin which was converted into the ketolactone, m. p. 60 

 to 63 , by chromic acid. This alcohol, therefore, also consisted of 

 a-terpineol. 



4* 



