ON THE CONSTITUTION OF CAMPHOU. olo 



Tliis sulpho-compound when treated with superheated steam breaks up 

 into isolauronolic and sulphuric acids.' 



(c) Action of Hiipuhromites on Ihe Isomeric Cianphoraiuic Acids. 



(i.) When a- camphoramic acid is warmed with sodium hypobromite it 

 is converted into aminodihydrolauronolic acid in accordance with the 

 equation 



COOH.C,H,4.CONH., + Br„ + 2KOH=COOH.C,Hi4.NH., 



+ 2KBr + C02 + H20. 



This amino-acid on treatment with nitrous fumes yields a hydrocarbon 

 CgH,4, ^y-lauronolic acid, CsHi.tCOOH, isocampholactone, CgHi402, 

 and an acid, melting at 180°, which has the formula C,)Hi.iO^. 



Hydroxydihydrolauronolic acid may be obtained from the ethyl ester 

 of the amino acid by means of nitrous acid and subsequent saponifica- 

 tion. On treatment with cold chromic acid mixture it loses carbon 

 dioxide and is converted into a ketone ; a behaviour which appears to 

 indicate that the hydroxyl group is in the /3-position with regard to the 

 carboxyl group. - 



(ii.) When /3- camphoramic acid is subjected to the action of hypo- 

 bromite it suffers a change similar to that which the a-acid undergoes, 

 and is eonvei'ted into amino- dihydrocampholy tic acid. This, on treat- 

 ment with nitrous acid, yields a hydroxy-acicl and subsequently campho- 

 lytic and isolauronolic acids. The elimination of the «Z/o-carbonyl group 

 in this manner, therefore, leads to results similar to those already 

 mentioned."* 



3. Oxidation of DEHyDROHOMOCAMPHORic Acid. 



When homocamphoric acid is brominated it Etffords a mono-bromo- 

 acid, as usual an a-derivative : the ethyl ester of this mono-bromohomo- 

 camphoric acid when heated with quinoline loses hydrogen bromide, and 

 the product, after saponification, yields, amongst other things, dehydro- 

 homocamphoric acid, naturally an a/3-unsaturated acid 





/CHBr . COOH /^CH . COOH 



-^CsH,3^ +HBr 



COOH X'OOH 



or writing it in accordance with what we know regai'ding the constitution 

 of homocamphoric acid (B. 2. b.) 



CH . CHBr . COOH C=CH COOH 



• -> 

 C . COOH C . COOH 



C C 



When the latter acid is oxidised with cold dilute permanganate it is 



' Walther, Ann. CkUn. Ph. [iii.], 9, 177 ; Kachler and Spitzer, Annalcn, 169, 

 170. and Pcrkin, Trans. Chem. Soc. 78, 790. 



-" Noyes, Amer. Chem. Journ., 16, 500 ; Bcr., 28, 547, and 29, 2::i20. 



» Noyes, Amcr. Chem. Jovrn., 16, 500; Bcr.. 27, 917, 28, 547, and 29, 2326, 



