ELISHA MITCHELL SCIENTIFIC SOCIETY, 77 



SOME ATTEMPTS AT FORMING HEPTYL- 

 BENZOL. 



F. P. VENABLE. 



Whilst examining the compounds of the heptane obtained from 

 Pinus Sabiniana, the possible preparation of this homologue of 

 benzol gave promise of an interesting research. This body would 

 be isomeric with the dimethyl-isoamyl benzol prepared by Fittig, 

 (Annalen. 141, 168), from bromxylol, isoamyl bromide, sodium and 

 ether and the methyldipropyl benzol prepared by action of sulphuric 

 acid upon a mixture of acetone and methylnormal-propylketone. 



The method of Fittig and Bigot was followed in the following ex- 

 periments; Pare brom. benzol (20 grm.) was mixed with 22 grm. 

 heptyl bromide and 8 grams of freshly cut sodium. To the whole 

 was added about an equal volume of absolute cither. The ether was 

 dried by standing over sodium, and then distilled over sodium. 

 This mixture was allowed to stand, showing very little action at the 

 end of a day or so. A reflux cooler was then attached, closed by a 

 chloride of calcium tube, and the whole heated on a water bath for 

 one day. The ether was then distilled off and the. remainder frac- 

 tionated. A portion coming over at a lower temperature was not 

 examined, but consisted doubtless of heptylen and unaltered ingre- 

 dients of the mixture. A portion easily solidifying gave, on rough 

 determination, the melting point 64°C, and proved to be diphenyl. 

 A very small portion boiled over 300^0, but it could not be 

 gotten pure enough nor in sufficient amounts for a closer examina- 

 tion. 



Again, as the iodide seemed much more capable of reacting than 

 heptyl bromide, it was substituted in a second experiment; 15 grams 

 heptyl oxide, 15 grams bromide benzol, and 6 grams of sodium were 

 taken, an equal volume of absolute ether added and the mixture 

 allowed to stand. The action was much more marked in this case, and 

 after standing about 24 hours, it was heated 2 hours on the water bath 

 filtered, with the addition of some ether, the latter distilled off and 

 the residue fractionated. The product seemed to be mainly of lowing 

 boiling point and diphenyl. A small portion boiling 225° and 238°C, 

 was saved for analysis, but on standing it deposited so much diphenyl 

 as to make further examination useless. 



It is probable that the body sought was formed along with the 



