— 99 — 



which acquires a greenish-violet colour when exposed to air. When 

 acidulated and diluted with ferric chloride there passes over with steam a 

 body which, when dissolved in ether, absorbs caustic potash solution with 

 violet coloration. Upon acidulation this body yielded a small proportion 

 of orange-coloured crystals, m. p. 164 to 166°, evidently «-hydroxythymo- 

 quinone. These crystals gave a reddish-purple colour with concentrated 

 sulphuric acid. Their aniline-derivative crystallised in deep violet needles. 



When the glycol is oxidised with neutral permanganate solution it yields, 

 in addition to a mixture of volatile acids (acetic acid, butyric acid ?), a 

 dibasic acid Ci Hi 6 O 5 , very sparingly soluble in water, m. p. 116,5 to 117°. 

 This is ascaridic acid, the silver salt of which is almost insoluble in 

 water. Its behaviour towards acetic anhydride, hydroxylamine, or semi- 

 carbazide shows that the molecule of the acid contains neither a hydroxyl- 

 nor a ketone-group, while its behaviour when titrated makes it clear that 

 it cannot be either an anhydride or a lactone. When heated above its 

 melting-point, methylheptenone 1 ) is apparently formed. When oxidised 

 the glycol yields yet another solid dibasic acid, melting at 186 to 187°, 

 to which Nelson assigns for the present the structural formula Ci Hi 6 O 6 . 



The product of conversion of ascaridol, which was prepared by us 

 at the time by heating a mixture of equal parts of ascaridol and cymene, 

 when shaken with 2% sulphuric acid under cooling, also yields the above 

 glycol, m. p. 62,5 to 64°, which when treated further by Schotten-Baumann's 

 method, yields a monobenzoate, m. p. 136 to 137°. This reaction proves 

 at the same time that in the reaction of ferrous sulphate with ascaridol 

 the absorption of the elements of water is attended by a rearrangement 

 of the molecule. The fact that ascaridol, therefore, cannot be regarded 

 as a true anhydride of the glycol Ci Hi 8 O 3 is further attested by its not 

 absorbing water when exposed to the action of 2% sulphuric acid or of 

 solutions of ferric oxide salts. 



From the above data the author concludes ascaridol to be a peroxide 

 possessing the following constitution: 



H. 3 C CH 3 





CH 







CH 





HC 



\ 



0, 



CH 



i 2 C 



o 



\ / 



\/ 



CH 

 CH, 



C 





Peroxid 



e. 



*) While distilling the acid C 10 H 1G O4, obtained by us in the course of permanganate 

 oxidation, we determined beyond doubt the formation of methylheptenone. 



