— 45 — 



Boiling point 94,5° to 96 ° (4 to 5 mm. pressure), 228° to 229 c 



(755 mm. pressure); di 5 o 0,9536; « D + I2 °5 / ; n D20° M9761. 



Combustion: 0,1424 gm. of the substance: 0,4108 gm. C0 2 , 









0, 



1352 



gm. 



H 2 0. 









Found 









Calculated for C 10 



H 16 







c 



H 



78,68 

 io,55 



/o 



/o 









78,95 % 

 10.52 % 







The analysis shows that the alcohol has the formula C 10 H 16 O. 

 A crystalline derivative has not yet been obtained. For the purpose 

 of ascertaining its constitution, it was attempted to produce oxidation 

 and reduction products. The oxidation with 1 per cent, permanganate 

 solution progressed so violently that it was necessary to cool with ice. 

 The final product formed a thick syrup which could not even in vacuo 

 be distilled without decomposition. For this reason we abandoned 

 for the time the further examination. By means of Beckmann's mix- 

 ture the alcohol was oxidised at the temperature of the water-bath, 

 on the one hand into an aldehyde C 10 H 14 O, on the other into an 

 acid of the melting point 13 2 . The first -named product could be 

 purified with the help of its bisulphite compound, and thus formed an 

 oil with a cumin-like odour, of the boiling point 23 5 . Its semicarbazone 

 of the melting point 19 8° to 198,5°, crystallising from alcohol in the 

 form of leaflets, served us for analysis: 



0,1733 gm. of the substance: 0,4028 gm. C0 2 , 0,1272 gm. H 2 0. 



Found Calculated for C 11 H 17 N 3 

 C 63,39 % 63,770/0 



H 8,15 o/ 8,21 o/ . 



The quantity of the acid was not sufficient for analysis. With 

 the view of reducing the alcohol to a saturated hydrocarbon, we heated 

 5 gms. each with 20 gms. hydriodic acid (spec. gr. 1,7) and 3 gms. 

 phosphorus in a sealed tube for 4 hours to 200°. In addition to 

 considerable quantities of resin, this resulted in a hydrocarbon readily 

 volatile with water -vapour, which had an odour like cymene. Its 

 boiling point lay at 172° to 179°. Oxidation with concentrated per- 

 manganate solution at the temperature of the water-bath, led, in 

 addition to terephthalic acid, also to p - oxyisopropylbenzoic acid of 

 the melting point 155° to 156°, that is to say, to compounds which 

 are formed on oxidation of p-cymene. In spite of all this we do not 

 at present wish to decide the question whether we had here to deal 

 actually with p-cymene, or with a hydrocarbon yielding the same 

 oxidation products. The occurrence of the same hydrocarbon was 

 also observed when we treated the alcohol for some time at ioo° with 



