— 199 — 



The synthesis of camphoric acid carried out by Komppa 1 ), Blanc 

 regards as illusory, in the first place because, upon repetition of the 

 process, the very first reaction (preparation of diketoapocamphoric 

 acid) was already a failure, secondly because Komppa has neglected 

 to follow up his preliminary communication, which was made nearly 

 six years ago, by a detailed publication. No doubt Komppa will 

 himself make a rejoinder to an attack delivered in such an unusual 

 manner. 



In conclusion Blanc asserts that the only problem in the chemistry 

 of camphor which yet remains to be cleared up is the conversion of 

 camphor into camphene and vice -versa, and hints that perhaps he 

 himself will take up this difficult question at a later date. 



Up to the present the only known homologues of camphor are 

 the monoalkyl compounds which have been prepared by various 

 methods by Baubigny, Minguin, and others. By treating sodium- 

 camphor (from camphor and sodium amide) with methyl iodide in 

 solution of ether or benzene, Haller and Bauer 2 ) obtained dimethyl 



/C(CH 3 )2 

 camphor CoH 14 < | which was recovered, in addition to about 



\co 



2 5 °/ of the weight of monomethyl camphor, from the product of the 

 above-mentioned conversion (b. p. 96 to 105 , 11 mm.) and which was 

 separated from the latter by converting this into its oxime. The pure 

 dimethyl camphor boiled at 106 (14 mm.) as a colourless liquid, 

 with an odour of camphor and fenchone. It possessed the following 

 constants: d^ 0,94708, Wd24° -j-9 2 >7°> m alcoholic solution -j-~9 2 >5°> 

 mol. refr. found 53,21, calc. for C 12 H 20 O" 53,31, My — M a found 

 1,30, calc. 1,27. The oxime of monomethyl camphor, prepared by 

 Crismer's method with zinc chloride and hydroxylamine hydrochloride had 

 a much higher b. p. than dimethyl-camphor (134 to 135 n mm.) 

 and could therefore easily be separated. Reduction of the last-named 

 body with sodium in a solution of absolute alcohol led to dimethyl 

 borneol, a viscous mass with a pronounced odour of borneol, congealing 

 in the cold; m. p. 18 to 20 ; b. p. 109 to in° (13 mm.). A few 

 crystals, m. p. 28 to 30 , with a rotation [«]d -(-32,4° appeared to 

 be a mixture of the two stereomeric dimethyl borneols. The urethane 

 of the new borneol crystallised in the shape of small needles, m. p. 

 111,5 to 112 , soluble in alcohol and ether, insoluble in petroleum- 

 ether, [«] D -{-29,5°. 



When dimethyl camphor was further treated with sodium amide 

 in a hot solution of benzene the well-known disruption of one of the 



*) Comp. Report April 1904, 98. 

 *) Compt. rend. 148 (1909), 1643. 



