i 9 7 — 



splits off readily, separated out first in the shape of clear crystalline 

 needles, m. p. 87 . When left to stand for some time longer, there 

 separated out from the solution masses of a porcelain-like appearance. 

 On one occasion such a solution of the glycol mixture yielded a large 

 crystal, melting at 9 6°, which may have represented either a eutectic 

 mixture of both forms, or a third stereomeric variety. The cis-trans- 

 glycol was prepared in the usual way by treating the residue of the 

 acetic ester solution, which contains both glycols, in benzene solution 

 with hydrochloric acid gas, with application of heat. By this treatment 

 the m-camphyl glycol which is still present is converted into dehydro- 

 camphyl glycol = bornylene carbinol XIV, m. p. 67 to 68° 

 (this body volatilises with steam); while the stable cis- trans-gly col remains 

 as a residue of steam- distillation and is isolated in the familiar manner. 



Oxidation of the two glycols with permanganate elucidated the 

 relations of each to the different borneol carboxylic acids. Corre- 

 sponding to the different behaviour of both acids during this oxidation 

 process, the glycols, too, yielded different products of oxidation, that 

 is to say, a's-trans~camphyl glycol (m. p. n 8°) yielded 84 per cent, 

 of the higher melting cis-frazzs-bomeol carboxylic acid, while m-camphyl 

 glycol (m. p. 8 7 ) yielded camphoric acid. In the case of the latter, 

 however, either through conversion into the cis- trans- variety, but more 

 probably because of the impure state of the m-glycol, a small quantity 

 of cis-trans borneol carboxylic acid was also produced. Hence, so far 

 as concerns their relationship as glycol and hydroxy acid, the following 

 are related: — 



Cfo-camphyl glycol, m. p. 87 , and cis- borneol carboxylic acid, 

 m. p. 101 ; aWram-camphyl glycol, m. p. 11 8°, and cis-frans-bomeQl 

 carboxylic acid, m. p. 171 . 



Bredt attaches to both papers a footnote communicating that 



camphononic acid, 



CH 2 CO 



I 

 CH3C.CH3 



I 

 CH 2 C(CH 3 ).COOH • 



which up to the present could not even be reduced by sodium in a 

 solution of boiling amylalcohol solution, was converted by electrolysis 

 into the corresponding camphonolic acid: 

 CH, CH-OH 



CH 8 

 CH 



C.CH3 



I 



C(CH 3 ).COOH 



m. p. 197 to 198 , and the latter, by the elimination of water, into 

 the corresponding camphonolic lactone, m. p. 161 . 



