— 140 — 



ing to Wallach and Wienhaus 1 ), the analogous formation of higher 

 homologues of camphene from camphor does not proceed equally well; 

 anyhow, the action of methyl magnesium iodide on the latter in 

 ethereal solution produced homoborneol, which was converted by loss 

 of water into homocamphene (b. p. 166 to 168 , m. p. 2 8°). The 

 principal object of this examination was the oxidation of the hydrocarbon 

 with permanganate. There was then formed an acid C 10 H 16 (O H) C O O H, 

 which was identical with the acid obtained from crude fenchene containing 

 camphor. This acid Wallach and Wienhaus designate as homo- 

 camphenylic acid, or better as a-borneol carboxylic acid, which as a 

 typical a-hydroxy acid could be readily isolated in the form of its 

 difficultly soluble sodium salt, and which was found to be isomeric with 

 the ^-hydroxy camphane carboxylic acid recently described by Bredt 2 ). 

 When heated rapidly, the acid in question melted at 179 , but 

 when heated very slowly already at 1 7 1°, probably owing to partial 

 decomposition in the neighbourhood of the melting point; Md — 34,8° 

 in methyl alcohol), — 30,72° (in ether). When heated with dilute 

 sulphuric acid and peroxide of lead, the acid was split up into camphor 

 (m. p. 1 75°, dextrorotatory; semicarbazone m. p. 23 7°, laevorotatory) and 

 carbonic acid. 



CCH, 



HX 



PLC 



CCH, 



C:0 



CH 



CH 



Homoborneol 



OH 



CH, 



C.CK 



C-CH Q 



C:CH 9 



CH 



CH 

 Homocamphene 



HX 



H C 



OH 



COOH 



CH 



Homocamphenylic acid 

 (a-borneol carboxylic acid) 



J ) Liebigs Annalen 353 (1907), 224. 



2 ) Tbidem 348 (1906), 205; Report October 1906, 135. 



