34U BROOKS. 



a neutral solution of the potassium salt, is amorphous when first precipitated, 

 but changes in a few hours to crystals. Under the microscope these crystals 

 proved to be rhombic plates, the acute angles of which are approximately 72°. 

 The substance decomposed with explosive violence when a combustion was 

 attempted. Two lead determinations gave 65.2 and 65.4 per cent of lead. Neutral 

 lead succinate contains, theoretically, 64.0 per cent of lead, but according to 

 Beilstein ° the salt exhibits a tendency to precipitate with a slightly basic com- 

 position, which would account for the slight discrepancy between the calculated 

 analysis and the results found. Lead succinate was made and its crystal angles 

 compared with the salt under investigation. The corresponding angles were 

 found to have the same values. 



One-half gram of the original substance was treated with 5 cubic centimeters 

 of alcohol and a small quantity of zinc chloride in hydrochloric acid. A few 

 drops of an ester were obtained which possessed an odor apparently identical 

 with that of diethyl succinate. 



It seems evident that succinic acid is present in the original crystalline 

 substance as a neutral ester. Therefore, if a carboxethyl group is assumed 

 to be present, the remaining alcohol radical must contain 10 carbon 

 atoms. 



Therefore the compound was saponified by boiling with an excess of aqueous 

 sodium hydroxide. Ten grams in 50 cubic centimeters of 5 per cent sodium 

 hydroxide solution were slowly distilled until 10 cubic centimeters had passed 

 over. This fraction possessed a strong odor, resembling that of carvol, or 

 perhaps isoeugenol, and owing to the presence of this substance in the distillate 

 the alcohol was not quantitatively determined. Its presence was qualitatively 

 shown by the iodoform reaction, the latter compound being slowly formed at 30° 

 and very quickly at 60°. The iodoform was recognized by its odor and the 

 characteristic habit of the crystals. 



Saponification of 2.0 grams of the compound with one-half the amount of 

 caustic potash theoretically required, yielded an acid substance which on evapora- 

 tion of its solution in ether gave a tough, resinous jelly which could not be 

 redissolved. 



Ten grams of the original compound were saponified at room temperature by 

 an excess of aqueous caustic potash. After standing 48 hours, 1 gram of the 

 original material was recovered by filtering and the alkaline filtrate extracted 

 five times with ether. The ether extract yielded about 0.1 gram of an oil having 

 an odor resembling that of carvol. A portion of the original solution was 

 slightly acidified with acetic acid and treated with phenylhydrazine acetate. 

 One-half of the resulting solution was gently heated on the steam bath and the 

 other portion placed in the ice box. Neither yielded a precipitate. The remaining 

 aqueous-alkaline solution was then acidified with sulphuric acid and extracted 

 five times with ether and 1.0 gram viscous oil were obtained which gradually 

 resinified. 



The substance or substances resulting from the hydrolysis or saponifica- 

 tion of the ketone, polymerize very readily, particularly in the presence 

 of alkalies. 



In one experiment the crystalline substance was saponified by heating for 

 about 10 minutes to 60° with alcoholic caustic potash; the solution quickly cooled 

 and the excess of potassium hydroxide neutralized by carbon dioxide. The 



" Handiuch d. Organischen Chenuie (1893), 1, 654. 



