Part IV.] Simonsen : Constituents of Indian Essential Oils. 
15 
oil was separated in the usual manner and the alkaline solutions 
reserved for further investigation (see below). 
The oil was repeatedly fractionated under diminished pressure 
(50mm.) when the following main fractions were ultimately obtained : — 
No. 
B. P. 
Yield per cent. 
I 
116-120“ 
8-10 
II 
170-175“ 
40 
III 
195-200“ 
40 
Fraction 1. — This fraction to which the original oil owes its smell 
was, on redistillation, found to boil constantly at 116°/52mm. and at 
197- 1997710mm. It had the following constants D|§o 0’9391, 
r465. These are in good agreement with those foimd by Stephan and 
Helle (Ber. 1902. 35. 2151.) who prepared p-methyl-/^ ®-tetrahydro- 
acetophenone from p terpineol and gave the following values 
Djgo 0’9435, No° 1’4742. Wallach and Eahn (loc. cit.) found that 
this ketone boiled at 205-206° and gave the following constant-. 
IQO 
I^go 0-940, Nu 1-4719. 
0-0964 gave 0 2754 CO2 and 0 0839 HoO, C=77-9, H=:9-7. 
CgHi40 requires C=78-2, H=10-l per cent. 
f -Methyl- /\f tetrahydroacetophenone semicarhazone crystallised from 
alcohol in glistening leaflets which melted at 165°. (Robe’-is loc. 
cit. p. 793 found 163-164°.) 
0-1287 gave 25-2cc.N2 at 15° and 710mm. N=21'3. 
CmH^,^ON3 requires N=21-5 per cent. 
p-Melhyl-/\f-teirahydroaGetoj)henone oxime crystallised from dilute 
methyl alcohol in needles melting at 50°. (Wallach and Rahn loc. cit. 
gave 51.5°.) 
0 0972 gave 0-2502 CO2 and 0-084 HgO, C=70-2, H=9-6. 
Cg Hjg ON requires 0=70' 6, 11=9-8 per cent. 
p-Methyl-/\^-tetrahydroacetO'p}ienone dibromooxitne crystallise 1 from 
alcohol in which it was somewhat sparingly soluble in rhombic plates 
which melted at 134-135°. (Wallach and Rahn loc. cit. found 130°.) 
0-116 gave 0-1385 AgBr Br=50-8. 
CgHjgONBra requires Br=51-1 per cent. 
A further proof of the identity of this ketone with p-methyl-A®- 
i etrahydroacetophenone was furnished by its conversion into p-tolyl 
methyl ketone when it was heated -with four times its volume of conc- 
entrated sulphuric acid on the water bath for a short time. The 
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