1869.] Mr. C. Schorlemmer on Octyl Compounds. 27 



Found. 



Calculated for C, H 15 Ag0 2 (1) (2) 



43-02 per cent. Ag. 42- 11 per cent. 43 87 per cent. 



(2) Derivatives of Octane from Methyl-hexyl Carbinol. 



The alcohol obtained from castor oil is easily converted into its corre- 

 sponding hydrocarbon by treating it first with iodine and phosphorus, 

 and acting upon the iodide thus obtained with zinc and hydrochloric acid. 



I have already described this hydrocarbon in a former communication ; 

 it boils constantly at 124° C. The octyl-chloride obtained from it has 

 only a faint orange-like smell ; it boils at 174°-176°. Heated with con- 

 centrated acetic acid and potassium-acetate to 200°, it is decomposed after 

 a few hours, octyl-acetate and octylene being formed in about equal quan- 

 tities, whilst the chloride obtained from petroleum gave about three times 

 more octylene than acetate. 



This acetate boils at 198°-202°, and has the same pear-like odour as 

 that described above. The alcohol prepared from it by heating it with 

 an alcoholic solution of caustic potash, had no constant boiling-point ; it 

 distilled between 180° and 190°; the greatest portion between 182° and 

 186 3 ; its odour is very much like that of methyl-hexyl carbinol. As I 

 had only about 4 grammes, I could not subject it to fractional distillation. 

 On oxidizing it with the chromic-acid solution, the greatest care was taken 

 to avoid rise of temperature, the solution being added very slowly until a 

 permanent brownish colour showed that a slight excess of chromic acid 

 was present, the vessel being all the time surrounded by cold water. In 

 order to have as decisive results as possible, I oxidised at the same time, 

 and under exactly the same circumstances, 4 grammes of methyl-hexyl 

 carbinol. The liquids were allowed to remain together for a day, and 

 were frequently shaken, then distilled, and the distillate neutralized with 

 sodium carbonate. 



The two results differed very widely ; methyl-hexyl carbinol was, as in 

 my former experiments, converted into methyl-cenanthol, a small portion 

 of which was oxidised further to acetic and caproic acids. The caproic 

 acid was separated by repeated distillation from the acetic acid, and neu- 

 tralized with ammonia. From this solution I purposed to prepare silver 

 salts by fractional precipitation, but only one precipitate was obtained. 

 0*1113 of this salt contained 0*0536 silver. 



Calculated for C 6 H u Ag 0 2 . Found. 



48-43 per cent. Ag. 48*16 per cent. Ag. 



The octylalcohol from the pure hydrocarbon yielded a large quantity of 

 an oily acid, and a smaller portion of a neutral oil, but not a trace of acetic 

 acid. The oily acid has the composition of caprylic acid ; it was analyzed 

 as the silver salt, which was obtained by fractional precipitations. 



1st Precipitate . . 0*3500 contained 0*1700 silver. 

 2nd „ .. 0*3090 „ 0*1335 „ 



