CRYSTALLINE CAMPHOR OF EUCALYPTUS OIL. 101 



the camphor. On continued boiling no crystalline product was 

 obtained. The acid solution was boiled continuously for two 

 days, and even then no crystalline product was obtained. On 

 addition of water no precipitate was formed. The nitric acid 

 was removed by evaporation, and to the small quantity remain- 

 ing, still in solution, water was added ; a minute quantity of a 

 camphoraceous substitute was obtained, but no crystals were 

 precipitated. This camphoraceous substance does not appear to 

 be the unaltered material, as it melted below 40° C. The filtrate 

 was evaporated to dryness on the water bath, water again added, 

 filtered, and this process repeated a few times. The filtrate on 

 again evaporating to dryness crystallised in microscopic crystals 

 on standing. These crystals were soluble in cold water to an acid 

 solution, which on addition of barium chloride and ammonia gave 

 no precipitate in the cold, but on boiling a precipitate was soon 

 obtained. This was filtered off, washed, treated with hydrochloric 

 acid and the solution agitated with ether. On evaporation of the 

 ethereal solution the residue showed microscopic crystals, this was 

 again crystallised from water. The product was a mass of micro- 

 scopic needles resembling camphoronic acid. No oxalic acid was 

 obtained. To be sure the crystals were camphoronic acid, that 

 acid was formed from ordinary camphor in the usual way, and 

 treated under exactly the same conditions ; the product resembled 

 in every respect that obtained from eudesmol, with the exception 

 that the melting point of the product from eudesmol (165 - 168°0.) 

 was a few degress higher than that from camphor, and that on 

 repeated crystallisation rather better defined crystals were obtained 

 with the acid from eudesmol. From the results by Aschan 1 and 

 by Perkin and Thorpe it is shown that the vcamphoronic acid 

 melts at a higher temperature than either d- or I- forms, and that 

 the i- acid has better defined crystals. It thus seems that the 

 acid derived from eudesmol will be found, when sufficient shall 

 have been obtained, to be ^-camphoronic acid. Eudesmol is readily 

 oxidised by chromic acid. The oxidation products of eudesmol 



1 Ber. 1895, xxviii., 16 and 224. 



