— 103 — 



water and distilled the resulting isolated oxygenous constituents with steam. 

 A strong menthone odour still adhered to these constituents, which were 

 treated with phthalic anhydride in order to isolate the alcoholic parts, 

 the result being an acid phthalate which was readily soluble in the usual 

 solvents. The crude product melted between 62 and 63°, the m. p. rising 

 to between 64 and 65° after recrystallisation from benzene. Finally, when 

 recrystallised from ether and chloroform, it gave m. p. 64,5 to 65,5°. The 

 alcohol which was regenerated from the phthalate constituted an oil with 

 an odour strongly reminding of secondary octyl alcohol: b. p. 57 to 58° 

 ^/smm.), d 15 o 0,8296, « D — 0°10', n D20 o 1,42652. When oxidised with bi- 

 chromate of potassium and sulphuric acid the alcohol gave rise to a ketone 

 of which the odour somewhat reminded of methylhexyl ketone. But it 

 was evidently not this ketone, as was proved by the fact that it gave no 

 reaction with neutralised sodium bisulphite solution. Moreover, the semi- 

 carbazone di4 not give the characteristic m. p. of methylhexyl ketone 

 semicarbazone. 



For the purpose of closer investigation we subjected a fraction 

 possessing "similar properties to that referred above to direct treatment 

 with phthalic anhydride. The characters of this fraction were as follow: 

 di 5 o 0,8521, « D — 52°26', n D20O 1,45991. The product wich was recovered 

 from the phthalate gave identical constants with the alcohol which was 

 prepared from the previous fraction: b. p. 56° (3V2 mm.), di 50 0,8279, 

 a D + 6° 17', n D20 o 1,42775. These constants underwent scarcely any change 

 as the result of distillation under ordinary pressure: b. p. 178,5 to 179,5°, 

 di 5 o 0,8276, « D + 6°26', n D20 o 1,42755. Oxidation with sodium bichromate 

 and sulphuric acid yielded a ketone which did not react with bisulphite. 

 The product which was regenerated from the semicarbazone (m. p. 117°) 

 possessed the following properties: b. p. 170°, di 5 o 0,8255, « D + 0°22', 

 n D2 oo 1,41556. Apart from its low optical activity, which appears to be 

 due to traces of impurity, the ketone possesses the constants of an ethyl- 

 n-amyl ketone which was isolated by us some years ago from French 

 lavender oil, and which were as follow: b. p. 169,5 to 170°, di 5 o 0,8254, 

 « D ± 0°, n D20 o 1,41536. A mixture of the semicarbazones of the two ketones 

 suffered no depression of m. p. The above facts may be held to afford 

 proof that the alcohol formed by us represents d-ethyl-w-amylcarbinol, 

 C 2 H 5 CH(OH)C 5 H 11 . 



We oxidised the alcohol with the calculated quantity sodium bichro- 



fiate and sulphuric acid, and obtained capronic acid, proof being afforded 

 y the b. p., the odour and analysis of the silver salt. 



0,1543 g. substance: 0,0757 g. Ag. 

 Found Calc. for C 6 HuAg0 2 



Ag 49,06 °/o 48,42% 



With phenyk'socyanate no phenylurethane was formed; a-naphthyh'so- 



