ELISHA MITCHELL SCIENTIFIC SOCIETY. 63 



OCTYL DERIVATIONS OF THIOPHEN. 



Preparation of octylthioplien. — This was prepared after the 

 method described for octylbenzoL 50 g. thiophen iodide, 50 g. octyl 

 bromide, and 22 g. sodium, together with twice the volume of ether, 

 were used. After the reaction the ether was distilled off on a water 

 bath and the remaining products of the reaction distilled at a gentle 

 heat. By fractionating the product obtained in this way, an oil, 

 boiling at 259— 263 , was gotten which had the same smell and taste 

 as octylbenzoL The analysis revealed only 12 p. c. sulphur, where- 

 as the calculated percentage is 16 32 p. c. Evidently the oil con- 

 tained dioctyl and it is difficult to effect a separation. Still after 

 several fractionatings of another portion of the crude product an 

 oil was obtained which boiled at 257— 259 , and an analysis of this 

 proved it to be pure octylthiophen. The oil is easily soluble in ether 

 and gave with phenanthrenchinon and sulphuric acid the Lauben- 

 heimer reaction. 



Analysis. — 0.1363 g. of ihe substance gave 0.1583 g. BaS04 corresponding 

 to 0.02174 g. S. 



Calculated for CSH1-.C4H3S — 16.32 p. c. ; found 15.95 p. c. 



Determination of Specific Gravity. — Weight of ihe substance in picnonieter 

 0.0820 g.; weight of water o.ioio; Specific Gravity (water 

 20.5') == 0.81 18 



Preparation of octyhnonobromthiophen. — This is prepared by 

 shaking octylthiophen with bromine water (1 mol.), washing the 

 product with alcoholic potash and water and then fractionating. In 

 this way an oil was gotten which boils at 285-290 . It is easily sol- 

 uble in ether, insoluble in water and solidifies to scales at 5°. 



Analysis. — 0.0935 g. yielded 0.06411 g. AgBr, corresponding to 0.0272 g. 

 Br. Hence found p. c. Br = 29.19; calculated for C4H0S. 

 CgHj,. Br p. c. Br = 29.09, 



Preparation 'of octylmono iod-thiophen. — The usual method mak- 

 ing use of iodine and mercuric oxide was pursued. 10 g. octylthio- 

 phen, diluted with an equal volume of ligroin (90 p. c), 10 g. iodine 

 and 11 g. mercuric oxide were used. The reaction proceeded very 

 slowly in the cold and was therefore hastened by a gentle warming 

 on the water-bath. After filtering off the mercuric iodide which 



