ELISHA MITCHELL SCIENTIFIC SOCIETY. 6$ 



hydrochloride and soda solution yielded an oil which solidified in 

 the cold to white crystals. By oxidation of the ketone it was hoped 

 that an oetylthiophen-mono-carbonic acid would be obtained. An 

 octylthiophendicarbonic acid however was obtained. This supris- 

 ing result is to be explained as follows : Since the octylacetthienon 

 distills difficultly with steam the distillation was stopped after some 

 hours. The residue in the flask which was considered identical with 

 the distillate was used for oxidation, after purification with animal 

 charcoal. This consisted for the most part of octyldiacethienon 

 C,HS.CsHi,.(CO— CH3J.(C0— CH3). 



To verify this some octyldiacetothienon was prepared pure from 

 10 g. octylthiophen (75 p. c), 10 g. acetylehloride and a sufficient 

 amount of aluminium chloride. After distilling with steam in order 

 to drive out dioctyl and other products the residue was exhausted 

 with ether purified by charcoal and the ether solution dried. After 

 evaporation of the ether there remained a yellow, thick syrup-like 

 liquid which solidified on being strongly cooled. It was easily solu- 

 ble in alcohol but not In water. 



Analysis. -0.1292 g. substance gave 0.1068 g, BaSO^ corresponding to 

 0.01466 g. S., or p. c. S = 11.35; calculated for CgHi^.C^HS. 

 (CH3C0)o p. c. S= 11.42. 



An alcoholic solution of the ketone treated with hydroxylamine 

 hydrochloride and sodium hydroxide yielded a nitrogenous product 

 which crystallized from alcohol. The crystals melted by 58*^. 



Preparation of octylthiophen dicarbonie acid. — The oxidation of 

 octyldiacetothienon was carried out with potassium permanganate 

 in the usual manner. 15 g. ketone, 40 g. potassium permanganate, 

 in 2 p. c. solution, and 40 g. potassium hydroxide were used. After 

 standing twelve hours and gently warming on the water bath the 

 reaction was completed. The manganese dioxide was then filtered 

 ofE and the filtrate acidified and exhausted with ether. On evapo- 

 rating the ether a solid with a disagreeable odor was left. Warmed 

 with a little water on the bath this bad odor was lost. The ether 

 solution of the residue, purified by animal charcoal, yielded a yel- 

 lowish, white substance with a fatty feel and strongly acid nature. 

 This acid showed as crystalline needles under the microscope, melted 

 at 185, with partial charring, is nearly insoluble in cold water and 

 soluble in hot water. 



Analysis. — 0.1456 g. substance gave 0.1159 g- barium sulpha. e or 0.01591 

 g. sulphur. Hence p. c. S = 10.91. 



Calculated for CgHi 7C4HS.(COOH)2 p. c. S =11.26. 

 7 



