~ anew. The final product, of the same b. p., contains no more camphor and is a 
| solubility in organic solvents; m. p. 72 to 73°; b.p. 179 to 180° (14 mm.). 
the former authors had committed when working on these camphor deri 
= hours’ heating the remainder of the methyl iodide is added, the heating is continue 
-monomethylcamphor only yields an oxime. For this purpose, the mixture is. heate 
he reported, with E. Bauer's on the preparation of mono- ad 
dimethyl campholic amide and dimethyl] campholic acid. Ina historical syn 
the preparation of the alkyl camphors the various mistakes are dealt 
then a description is given how the different alkyl camphors. and their oe 
obtained. il Case 
In a flask with reflux condenser a mixture of 152 g. camphor, 500 g. aye 
benzene, and 40g. finely-powdered sodamide is introduced. Ammonia ise 
the cold, and the mixture is heated for 5 hours on a water-bath. . Methyl 
(?/; molecule), dissolved in ether or benzene is then added drop by drop. After Dey 
r ‘/2 hour and the mixture allowed to cool down. The cold reaction-mixture — 
ae into water whereby sodium iodide and the hydriodides of methylated amin 
are dissolved; the supernatant liquid is drawn off, washed and distilled in orde’ 
drive off the solvent. The residue is distilled in vacuo; b. p. 95 to. 110° (1 mm.), t the, 
distillate is a mixture of camphor, mono- and dimethylcamphor which is. ‘methylated 
mixture of mono- and dimethylcamphor which may be separated by oximation, since 
in twice its volume of alcohol, with zinc + hydroxylamine chlorides for three day 
Monomethylcamphoroxime (V) boils at 134 to 135° (11 mm.); dimethylcamphor (I) at 106° © 
(11 mm.); d?5 0.94708; [@]p.s0 + 97°50’; np 1.47187. The latter ketone is likewise stab oe 
towards all the other reagents for ee In alcoholic solotion, it is reduced 
sodium to d-dimethylcamphol (dimethylborneol) (Il), a product smelling of borneol a ¢ 
consisting evidently of a mixture of @- and @-dimethylcamphol. The a-isomeride whic 4 
separates first from the mixture melts at 56 to 57°; [e])>-+55°4' (0.2095 g. in 10 cc. 
alcohol); [«]p + 60° 4’ (0.1482 g. in 10 cc. benzene). The -dimethylcamphol remai 
liquid and was naturally not chemically pure. By action of sodium amide, in benz 
solution, on dimethylcamphor, dimethylcampholic amide (Ill) results, a body of ea 
treating the amide with sodium nitrite, dimethylcampholic acid (IV) is OBtAREE: m. -P 
to 74°. : 
a-Monomethylcamphoroxime (V) melts at 60°; b. p. 134 to 1350 (11 inet [ap +23. 1 
(0.488 g. in 10 cc. absolute alcohol). Since Glover‘) quotes different properties for th v4 
oxime, the authors converted the oxime into the carbanilide (phenylurethane). 
body (VI) was obtained in an inactive as well as an active form ({¢]p + 24.89 
in 10 ¢ cc. absolute alcohol)’ which both method about 112 to 113°; the mixtur 
Siacnter so 
eS a ee ee ee ee a — 
presence of which might have explained the variations from ‘Gove: 's st 
a-Methylcamphoroxime prepared differently melted ae at A 
1915, 97. — 2) Annal. de Chim. IX. 8 ie AFF. 
