— 136 — 



keeps fairly well in the light. The camphyl glycol produced by the 

 Farbwerke vorm. Meister Lucius & Bruning 1 ), which consists 

 of two stereo-isomeric glycols, cis- and trans-glycol, shows, according 

 to Bredt, a very near relationship to the borneoi carboxylic acids 

 described. Dehydro camphyl carbinol formed from cis- and trans-camphyl 

 glycol by heating or treatment with mineral acids, corresponds to all 

 appearances in its constitution with camphene carboxylic acid; it is 

 moreover, like the latter, volatile with water vapour. 



The synthesis of isolaurolene and isolauronolic acid has long been 

 known in principle, but it has found practical application only in the 

 synthesis of a , a - substituted dimethyladipic acid. G. Blanc 2 ) con- 

 verted it, by heating with acetic anhydride, into its anhydride, 

 from which is formed by slow distillation at ordinary pressure di- 

 methylcyclopentanone, and from the latter by condensation with methyl- 

 magnesium iodide a tertiary alcohol: 



C H, C H„ C H„ C H„ 



CH 2 

 CH 9 



CO 



CH 



CE 



CH 3 

 OH 



CH 2 CH 2 



which on distillation at ordinary pressure is split up into water and 

 a hydrocarbon identical with isolaurolene: 



C H 3 C H 8 C H q C H, 



CH, 



CH, 



/CH 3 

 C< CH 2 



\OH =H 2 + 



CH 9 CH, 



C-CH, 



CH 



This hydrocarbon is exidised with potassium permanganate to di- 

 methylpentanone carboxylic acid (m. p. 4 8°) 



CH, CH a 



CH 2 



CH 9 



CO — CHg 



COOH 



1 ) German Patent 123909; Friedlander, Fortschritte der Teerfarbenfabrikation 

 und verwandter Industriezweige VI., p. 1268. 



2 ) Compt. rend. 142 (1906), 1084. 



ation 



