— 6o — 



The oil of Persea gratissima Gaertn. had already been examined 

 in our laboratory in 1894 1 ). At that time methyl chavicoi was 

 already recognised as the principal constituent of the oil. Although 

 the conversion of this substance into anethol by heating with alcoholic 

 potash did not then succeed, owing to the breaking of the vessel, it 

 was yet possible to obtain anisic acid of the m. p. 183 , by oxidation 

 of a small quantity of the oil thus treated with potassium perman- 

 ganate. The renewed examination has confirmed the presence of 

 methyl chavicoi as principal constituent of the oil. Besides this, d- 

 pinene was detected in the first runnings of the oil (b. p. to 83 ° at 

 5 mm. pressure; «d -{- 23°45 / ). When distilled once at ordinary pressure 

 over sodium, the bulk of this fraction passed over between 157 and 

 165 . By the action of amyl nitrite and hydrochloric acid in a solution 

 of glacial acetic acid, pinene nitrosochloride was produced from it, 

 whose benzylamine compound, after being once recrystallised from 

 alcohol, showed the m. p. 123 . 



The principal fraction of our oil had the peculiar odour of methyl 

 chavicoi, and also very nearly the properties of the pure body: 

 di5° 0,9712; « D ±o°; n D16 o 1,52243; b. p. 83 (at 5 mm. pressure). 

 By heating it for one hour with alcoholic potash, the bulk of the oil 

 was converted into anethol solidifying at -|~ 13,8°. Heating this 

 crude anethol once more for one hour with caustic potash, raised 

 the sol. p. only to -j- 14,2°. This product when distilled in vacuo 

 (3 mm. pressure) passed over entirely between 85 and 87 . The 

 principal fraction (b. p. 86,9 to 87,2°, 3 mm. pressure) had the pure 

 taste and odour of anethol, and solidified at -[-17,7°, whilst the 

 portions first passed over only solidified at -)- 8,6°, and consequently 

 still contained some methyl chavicoi. 



The fraction of the last runnings of the original oil (b. p. 84 to 

 8 5° at 5 mm. pressure) when distilled once more passed over almost 

 completely at 8o° (5,5 mm. pressure), and had d^o 0,971; «d + o°; 

 n Di5° 1*52278. It did not solidify in a freezing mixture, and there- 

 fore consisted also entirely of methyl chavicoi, which was also 

 proved by oxidation. When treated in the cold with 1 per cent, 

 permanganate solution, it yielded first of all a solid acid, which showed 

 still an indistinct melting point. It commenced to soften at 8i°, but 

 was only completely melted at about 160 . By fractional crystallisation 

 from hot water two acids could be isolated from it, of which one 

 (which appeared to be formed in the bulk, and which was readily 

 soluble in water) formed colourless leaflets with a silver lustre, which 

 finally melted between 84 and 85 (homoanisic acid = methoxyphenyl 

 acetic acid). The other acid produced in smaller quantity, and more 



*) Report October 1894, 69. 



