6o JOURNAL OF THE 



OCTYLBENZOL. 



E. A. VON SCHWEINITZ. 



With regard to the discussion over the constitution of Thiophen, 

 it is of interest to prove whether two compounds, formed by intro- 

 ducing two different substituting groups in inverted order, e. g., 

 methyloctyl thiophen and octylmethyl thiophen, would show the 

 same characteristics. 



To settle this question it was first necessary to prepare octyl thio- 

 phen, which can easily be done by following V. Meyer and H. Kreis' 

 description of the preparation of the homologues of thiophen. The 

 change of this into the monois octylthiophen and then into the oc- 

 tylmethylthiophen should yield ouv^ of the compounds in question 

 and the introduction of the octyl group into thiotolen should give 

 the other. According to previous researches into the position of the 

 iodine in the thiophen group, the two .substituting groups have the 

 j8-position. The question whether the two compounds are identi- 

 cal must be settled by an accurate comparison of the two. 



Whilst engaged upon this question it was observed that no com- 

 pound corresponding to octylthiophen was known in the benzol 

 series, though isomers and nearly allied bodies occur. Dibutylben- 

 zol has been described by Goldschmidt (Ber. d. deutsch. Chem. 

 Ges. XV, 1067), obtained by the action of butylalcohol on benzol in 

 the presence of zinc chloride and Beran (Ber XVIII, 131) obtained 

 by the action of octylalcohol on anilin the amido derivative of oc- 

 tylbenzol. I have found that octylbenzol can easily be prepared by 

 the method of Fittig, which, according to V. Meyer, succeeds with 

 all bodies having a normal side chain, and the larger the molecule 

 the better. 



It seemed advisable to prepare and study this octylbenzol before 

 going on with the preparation of octylthiophen. 



PREPARATION OF OCTYLBENZOL. 



The preparation of the octylbenzol was carried out in accordance 

 with the direction of Fittig (Ann. Chem. Pharm. 144, 278), 24 g. 

 Brombenzol, 31 g. normal octyl bromide, 11 g. sodium and the double 

 volume of waterfree ether were used. The octyl bromide was pre- 

 pared by the action of bromine and phosphorus on octylalcohol 

 after the method of Zincke (Ann. Chem. Pharm. 152, 5). 



