— 134 — 



to the other difficulties of the production of synthetic camphor on a 

 large scale, which are specially due to the great cost of the crude 

 material, it remains questionable whether synthetic camphor will be 

 able to compete permanently with the natural product. 



A. Haller and J. Minguin 1 ) have examined the products resulting 

 from the action of sodium isobutylate and propylate on camphor at 

 high temperatures. When heated for 24 hours in an autoclave to 

 220 to 230 °, a butter-like reaction-product is formed, from which 

 water dissolves sodium isobutylate, ether dissolves an oil. The latter 

 when submitted to fractional distillation yielded isobutyl alcohol, borneol 

 ("camphol"), and a syrupy oil of the b. p. 235 to 255 , from which 

 on cooling to about o° after some days isobutyl borneol, C 14 H 26 O 

 could be separated off; m. p. 55 ; Md-|- 20°7 / in alcoholic solution; 

 acetylation yielded an ester of the b. p. 13 5 (20 mm. pressure) from 

 which after saponification the original oil was regenerated. Isobutyl 

 borneol _ __ 



/ tH 3 



7 CH.CH 2 • CH( 

 C 8 H / I \CH 3 



x CH.OH 



is not attacked in acetone solution by permanganate in the cold, but in 

 benzene solution it is converted, by shaking for 12 hours with a sul- 

 phuric acid solution of permanganate, into isobutyl camphor (m. p. 2 8°; 

 Md in alcoholic solution -|- 72°4 / ), which after heating in a tube to 

 ioo° with equimolecular quantities bromine and treating the reaction- 

 product with alcoholic potash, yields isobutylidene camphor 



C 8 H / I 



x co 



b. p. 145 (10 mm. pressure); Md -f~ I I 4°4 / - The l att er is con- 

 verted by the action of concentrated nitric acid, or of amylnitrite and 

 nitric acid, into its nitrosate ; m. p. 17 8° with decomposition; Md (acetone 

 solution) -f-93 . With dilute potash liquor the nitrosate is converted 

 into isonitroso isobutyl oxycamphor, 



NOH 



.COH.C.Cg^ 

 C 8 H 14 < I 



m. p. 8 5 . If sodium isobutylate is allowed to act under normal 

 pressure at the reflux condenser on camphor, the same reaction takes 

 place, only that as principal product isobutylidene camphor is formed 



1 ) Compt. rend. 142 (1906), 1309. 



