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Mr. J. E. Marsh. Researches on the [Dec. 5, 



II. "Researches on the Chemistry of the Camphoric Acids." 

 By J. E. MARSH, B.A., Demonstrator of Organic Chemistry 

 at the University Laboratory, Oxford. Communicated by 

 Professor Odling, F.R.S. Received August 15, 1889. 



For some time past I have been engaged in the study of some deri- 

 vatives of camphor, with the view of determining, if possible, with 

 •some degree of certainty the constitution of that body. I do not pro- 

 pose to enter now into airy account of the present state of our know- 

 ledge as to the chemistry of camphor, but at once to bring forward 

 something of my own experience on this subject. 



Of part of the results which I have obtained I gave a brief 

 account at the meeting of the British Association last year at Bath. 

 This account had reference chiefly to some further evidence of the 

 relationship of camphor to hexahydrometaxylene, and to the products 

 of oxidation of camphoric acid by means of an alkaline solution of 

 potassium permanganate. These researches were not published, and 

 are not even yet completed. 



On the other hand, I have made some additional experiments which 

 I am anxious to bring forward now, as it may be some time before 

 the whole series is finished. 



The experiments to be described have reference to certain pro- 

 cesses which resulted in the preparation of a new camphoric acid ; 

 and the remarkable properties of this acid contrasted with those 

 of the ordinary camphoric acid throw considerable light on the 

 nature of the isomerism subsisting between these bodies. 



Camphoryl Chloride. 



I have had occasion to prepare considerable quantities of cam- 

 phoryl chloride, C 10 H 14 O 2 Cl 2 , by the action of pentachloride of phos- 

 phorus on ordinary camphoric acid. Camphoryl chloride was obtained 

 originally by Moitessier (' Compt. Rend.,' vol. 52, p. 871), but only 

 as a crude product, which he found to decompose on distillation. The 

 substance may, however, be readily purified by distillation in vacuo , 

 when it distils about 140° C. under 15 mm. pressure. There appears 

 to be no difference in the product of the reaction however much penta- 

 chloride of phosphorus is used, provided the temperature be not 

 raised above that of boiling water. 



Chlorocamjphoryl Chloride. 



If, however, camphoric acid is heated with a large excess of penta- 

 chloride of phosphorus on a sand-bath in a flask provided with a 

 reflux condenser, a new body of the formula C 10 H 13 Cl 3 O2, viz., chloro- 



