1889.] 



Chemistry of the Camphoric Acids. 



7 



camphoryl chloride, is obtained. A further account of this body and 

 its transformations I will reserve for a future publication. 



The camphoryl chloride was prepared in order to attempt to reduce 

 it to the lactone similar to the lactones obtainable from phthalyl and 

 succinyl chlorides. It was not found possible to obtain a lactone 

 under the various conditions of experiment from time to time 

 adopted. 



Action of Water on Camphoryl Chloride. 



Circumstances, however, led to the consideration of a more simple 

 reaction, namely, the action of water on camphoryl chloride. 

 Moitessier had stated that this reaction was such as to give back 

 camphoric acid. He means, presumably, the original dextro-rotatory 

 acid, as he does not mention more than one. This acid is, in fact, 

 formed, as will be shown subsequently, but only in very small quan- 

 tity, and can only be separated from and recognised among the other 

 products of the reaction after special treatment. 



If camphoryl chloride obtained from ordinary dextro- camphoric 

 acid is added gradually to about ten times its weight of hot water, 

 there is formed about equal quantities of camphoric anhydride and a 

 new camphoric acid, which rotates the ray of polarised light to the 

 left. These two bodies are contained in the precipitate after cooling, 

 and form by far the greater part of the product. Besides these, there 

 is formed a small quantity of another substance more soluble in water, 

 which separates from a strong hot aqueous solution as an oil, after a 

 time solidifying. This is a mixture of the ordinary dextro-camphoric 

 acid with the new laevo-rotatory acid. I will refer to this again 

 later. 



The camphoric anhydride and Isevo-camphoric acid obtained in thi ( 

 reaction are readily separated by treatment with carbonate of soda in 

 the cold, by means of which the laevo-acid is dissolved, leaving the 

 anhydride untouched. This anhydride is converted into the ordinary 

 dextro-rotatory camphoric acid by solution in hot caustic soda and 

 precipitation by hydrochloric acid. I have been able to confirm de 

 Montgolfier's observation that the camphoric acid obtained from the 

 anhydride has a specific rotatory power of over +48°. I have found 

 Hd = +48'25°. (The determinations of rotatory power have been 

 made throughout with a Laurent half-shade polarimeter, kindly lent 

 me by Dr. Haldane, of the Physiological Department.) 



Properties of the Lavo-carnphoric Acid. 



The lsevo-rotatory acid obtained above has a rotation about equal, 

 and of opposite sign to the dextro-acid. I have found [a] D = — 48'09°. 

 I am convinced, however, that these two acids are not optically 



