— 98 - 



wanting, owing to the impossibility of conceding the prices which are 

 demanded for the raw material. Apparently the consumers are not at all 

 troubled by the total absence of this particular variety. 



A paper by E. K. Nelson 1 ) on chenopodium oil makes a valuable 

 contribution to our knowledge of the chemical characteristics of the body 

 CioHi 6 2 which was isolated by us from this oil some years ago 2 ), and 

 to which we gave the name of ascaridol. The author examined four 

 samples, which he had procured in Maryland, the producing country. The 

 constants of these samples were as follow: d 25 o 0,955 to 0,9691, « D — 5,4 

 to 8,8°, n D25 o 1,4723 to 1,4726, sol. in from 3 to 7 vols. 70% alcohol. A 

 fifth sample, at least one year old, which was used for the purposes of 

 the examination recorded below, gave: d 25 o 0,9694, « D — 0,35°, n D20 o 1,4780, 

 sol. in 3 vols. 70°/ alcohol, acid v. 0, ester v. 5,0. In addition to ascaridol: 

 b. p. 96 to 97° (8 mm.), d 20 o 0,9985, « D -f 0,7°, n D20 o 1,4719, Nelson isolated 

 cymene and <i-camphor, both of which bodies had already been detected 

 by us at the time as constituents of the oil. The results obtained by 

 shaking ascaridol with saturated solution of ferrous sulphate are, however, 

 of particular interest. At ordinary temperature this peculiar reaction 

 proceeds with such violence as to decompose the ascaridol, the tempera- 

 ture rising considerably with evolution of a combustible gas 3 ). Isopropyl 

 alcohol is also formed as a product of reaction and was isolated from 

 the syrupy product of conversion by steam-distillation and identified as 

 acetone by oxidising it with chromic acid (dibenzylidene acetone, m. p. Ill 

 to 112°). Below 35° the reaction proceeds normally and without de- 

 composition. In these conditions ascaridol adds the elements of the 

 water and is converted into a glycol, CioHi 8 3 which, when benzoated 

 by Schotten-Baumann's method, yields a solid benzoate, m. p. 136 to 137°. 

 Saponification of this ester yields the pure glycol, in the form of a 

 colourless and odourless, syrupy oil, b. p. 271 to 272°, from which, after 

 prolonged standing in a vacuum desiccator solid crystals, m. p. 62,5 to 64°, 

 are precipitated. The glycol Ci Hi 8 O 3 gave the following constants: 

 d 20 o 1,0981, a D +0, n D20O 1,4796, mol. refr. 48,63 (calc. 48,65). The fact that 

 the body Ci Hi 8 O 3 possesses a second OH-group is shown by the formation 

 of a dibenzoate, which occurs when the glycol is heated for 2 hours with 

 benzoic anhydride to 150°. From alcohol, the ester crystallises in needles, 

 m. p. 116,5 to 117,5°. 



In all probability the third oxygen-atom is contained in the molecule 

 Ci Hi 8 O 3 in the form of oxidic oxygen. When the glycol is melted with 

 caustic potash or boiled with sodium, it is converted in part into a compound 



l ) Journ. Americ. chem. Soc. 33 (1911), 1405. 

 2 y Report April 1908, 109. 



3 ) The occurrence of a combustible gas as a decomposition-product of ascaridol was 

 first noticed by us at the time. 



