1868.] 



Capryl Alcohol from Castor -oil. 



377 



this fraction nor any other distillate contained an acetone, as none com- 

 bined with hydrogen-sodium sulphite. According to Chapman, the liquid 

 boiling at 170° consists chiefly of heptyl alcohol*. In order to isolate 

 this alcohol, I acted upon the Hquid boiUng between 160°-175° with iodine 

 and phosphorus. The product, subjected to fractional distillation, was 

 found to consist of isoctyl iodide, boiling at 210°-2I5°, and of hydrocar- 

 bons, distilling below 160°; the portion which came over between 160° 

 and 210° was very small, and diminished after each further distillation. 

 This shows that no heptyl alcohol was present, and that the original liquid 

 boiling at 170° was a mixture of isoctyl alcohol and hydrocarbons, which 

 could not be separated by simple fractioning. 



To obtain the oxidation products of isoctyl alcohol, I acted upon it with 

 a solution consisting of 3 parts of sulphuric acid, 2 parts of potassium 

 bichromate, and 10 parts of water, the reaction being moderated by sur- 

 rounding the vessel with cold water. As soon as no further action was 

 observed, the liquid was distilled. The distillate consisted of an aqueous 

 liquid, which had a slight acid reaction, and a light oily fluid ; it was neu- 

 tralized with sodium carbonate, and the oil treated again with the oxidizing 

 mixture, which, however, had hardly any action upon it in the cold. This 

 oily liquid is methyl oenanthol ; it has the characteristic odour of that 

 compound, and when shaken with a concentrated solution of hydrogen- 

 sodium sulphite, solidifies to a mass of pearly white crystals. These were 

 dried between blotting-paper, and decomposed by a dilute solution of caustic 

 soda. The oil which separated was dried over calcium chloride ; it dis- 

 tilled completely between 170°-172°, the boiling-point of methyl oenanthol 

 being 171°. 



In order to oxidize this compound further, it had to be heated with the 

 oxidizing mixture, when a slight evolution of carbon dioxide was observed. 

 The acid distillate was neutralized with sodium carbonate, and the acetone 

 unacted upon treated again as before. The different solutions of the so- 

 dium-salts were evaporated, and the solid residue decomposed by diluted 

 sulphuric acid. An oily acid separated, which, after drying, distilled at 

 198°-200°, which is the boiling-point of caproic acid, the characteristic 

 odour of which it also exhibited. To place beyond doubt that it was 

 really this compound, a portion of it was neutralized with ammonia and 

 precipitated by silver nitrate. A white curdy precipitate was obtained, 

 which was nearly insoluble in cold water, and only slightly soluble in 

 boiling water. It did not darken either by exposure to the light or to a 

 temperature of 100°. From the hot saturated solution it separated as a 

 crystalline powder ; nor could I obtain it in definite crystals by evaporating 

 the solution in vacuo. 



(1) 0-2407 of this salt gave O'l 170 silver. 



(2) 0-3720 gave 0-1810 silver. 



Journ. Chem. Soc. New Ser. vol. iii. p. 295. 



