506 Hydrocarbons 
tion it was universally accepted that saturated aliphatic hydro- 
carbons are not attacked by this reagent. 7 
The observation of the Russian chemists has not been followed 
up bya study of the products of oxidation, nor has it been extended 
to observations on other hydrocarbons. The present work was 
undertaken with the object of obtaining the lacking information. 
Since few tertiary hydrocarbons are readily accessible the work 
naturally fell into two parts, one directed towards the synthesis 
of tertiary aliphatic hydrocarbons and the other to the study 
of their behavior towards potassium permanganate. The work 
is reported in its present incompleteness because one of the 
authors has accepted a commission with the United States 
Army. 
The most practical and economical way for the preparation of 
the hydrocarbons was found to be the one based on the reduction 
of acids obtained by the malonic ester synthesis. In a general 
way the routine adopted in the work of Levene and Allen was also 
followed here. However, a marked improvement was introduced 
in the method of the reduction of esters to the corresponding alco- 
hols. The details are given in the experimental part. Up to the 
present there were prepared all the intermediate substances leading 
up to 2-butylhexane as well as the hydrocarbon, also all the in- 
termediate products leading up to 4-butyloctane but not the 
hydrocarbon. 
Regarding the behavior of 2-butylhexane towards perman- 
ganate it -was found that it readily underwent oxidation in an 
alkaline solution of the reagent. However for the purpose 
of the study of the products of oxidation, special conditions 
had to be chosen. Namely, it was found that when the oxi- 
dation was permitted to proceed at moderately elevated tem- 
peratures (between 80-90°C.), the only oxidation products that 
could be detected were formic and carbonic acids. On the other 
hand when the oxidation was conducted at a temperature in the 
neighborhood of 25°C. evidence was obtained of the formation 
of butyric acid. This acid was identified as its silver salt. The 
present experiment was carried out only on a small sample of 
material. It is intended to continue the work on a larger scale. 
The experience gained up to the present is important in as far 
as it indicates the conditions of experimentation which will per- 
