407 



Preparation of Veratric Acid. 



Six grams of the large fraction were first treated with neutral permanganate 

 of potassium, and the oxidation finally completed in an acid solution. The product 

 was then cooled and extracted with ether. The ether was distilled off, and the 

 crystalline mass which remained, repeatedly re-crystallised from hot alcohol. The 

 melting point of the crystals was 178-179° C. The yield was excellent. The 

 crystals were but slightly soluble in water, readily in ether, and less so in cold 

 alcohol. An analysis gave the following : — 



0-1512 gram gave 0-3284 gram CO.^, and 0-0756 gram H.^0, 

 C = 59"23 per cent, and H = 5-55 per cent. 



QHiuOj requires 59-34 C. and 5-49 per cent. H. 



0-1504 gram acid dissolved in excess of decinormal NaOH and titrated 

 back had required 8-3 c.c. of the soda solution to neutralise. This 

 represents a molecular weight of i8i-2. QHioOj = 182. 



Veratric acid is, therefore, the acid formed on oxidising the oil. 



When the oil was boiled with hydriodic acid, with precautions as with 

 Zeisel's method, an abundance of silver iodide was obtained, indicating the 

 presence of methoxy groups. 



From the results of the physical properties, the analysis, the formation of 

 the bromide, and the preparation of the veratric acid, it is evident that the greater 

 portion of the oil obtained from the timber of the " Huon Pine" is the methyl 

 ether of eugenol (allyl veratrol), QH3-C3H,(i)-OCH3(3)-OCH,(4), and that the 

 odour of the wood is largely due to that substance. The phenol, eugenol, was 

 not detected in the oil. 



The higher boiling portion of the oil gave the colour reactions for cadinene, 

 but, with the small amount of a possible sesquiterpene present in the oil, no satis- 

 factory reaction was obtained, and the crystalline hydrochloride for cadinene 

 was not formed. The identity of a possible sesquiterpene thus remains in 

 abeyance. 



