Olf THE CONSTITUTION OF CAJVIPfiOR. 



311 



catbon is not attended with any isomeric change is proved by the fact 

 that it yields, on treatment with acetyl chloride in presence of aluminium 

 chloride, a ketone identical with that obtained by the action of zinc 

 methide on isolauronolic chloride : 



CMe^.OMe 



/ j 



CH, ' 



\ 

 CH,— COOH 



CMe.,.CMe 



CH. 



CH,-CH 



CMe.,.COMe 



/ 

 CH.. 



\ 

 CH.,.COOH 



4- 



CMea.CMe 



/ 

 CH, 



\ 

 CHo— C.COCl 



CMea-CMe 



/ I 



CH., 



\ ' 



CH.,— C.COMe ' 



The formation of isolauronic acid, during the oxidation of isolauronolic 

 acid with faintly alkaline permanganate, hithei'to so difficult to undei'stand, 

 is easily explained by the use of the foregoing formula, as the first action 

 of the oxidising agent would result in the formation of an acid derived 

 from a 1 : 5-diketone, a class of compounds Tery prone to undergo con- 

 densation in alkaline solution, that is to say, under conditions similar to 

 those in which isolauronic acid arises : - 



Bouveault's formula for isolauronic acid has been submitted to searching 

 tests by Blanc, with the result that no reasonable doubt of its correctness 

 can any longer be entertained. The following observations are so 

 important as to warrant somewhat detailed description. 



Isolauronic acid is reducil^le by two stages : first to dihydroisolauronic 

 acid, which is of a ketonic nature ; and secondly to the tetrahydro-acid, 

 which must be a y or 8-liydroxy acid, as it affords a lactone with great 

 readiness : 



CMe,— CO 

 -> CH., CH, 



CH2— CH.COOH 



Dihj-dro-acid. 

 ,CMeo— CH.OH CMeo.CH— 



CMe.,— CO 



CH, 



\ 

 CH 



CH, 

 -C.COOH 



Isolanronic Acid. 



-> CH, CH, 



\ 

 CH,— CH.COOH 



Tetrahydro-acid . 



CH, CH, 



\ / 



CHa— CH— C0 



Lactone. 



' Blauc, JMl. Soc. Clilm. (iii.), 19, 69!i. 

 -' Bouveault, Bull. Soc. Ch'm. (iii.), 17, DO!*. 



