Conversion of Bcnsol-PJicnol. 21 



Summary of Results. 



The above experiments have shown that primary and 

 secondary amines, together with carbonized substance, are 

 produced when isobutylphenol, isoamylphenol, thymol and 

 carvacrol are heated to 320°-36o° with an excess of zinc- 

 ammonium-bromide and ammonium-bromide or with the chlo- 

 rides of zinc and ammonium. 



Better results were obtained by using the bromine com- 

 pounds. 



The percentage of amines reached its maximum — seventy 

 per cent — with carvacrol ; the three other phenols yielding 

 only forty-five to sixty per cent of the original substance. 



In a manner similar to that used with the cresols and 

 xylenols, these more complicated homologues of benzol- 

 phenol have been converted into amines ; but the bases so 

 obtained have not formed chemical combinations so readily 

 as the bases obtained from the phenols of simpler form. 



So far as I know, the primary base — carvacrylamine — 

 has not been previously described.^ When freshly distilled, 

 it is an almost colorless oil of a disagreeable odor ; boiling 

 point, 24i°-242°. In a freezing mixture it became solid with 

 an indistinctly crystalline structure. Its derivatives are 

 beautifully crystalline. For further identification of the 

 amine, its platinochloride and acetyl and benzoyl derivatives 

 were studied. 



The secondary bases, namely, diphenisobutylamine, diphe- 

 nisamylamine, dithymylaniine and dicarvacrylamine, are oily 

 liquids which boil above 300°, are nearly colorless when first 

 distilled, but color on exposure to the air. The dicarvacryl 

 and dithymyl bases have a most agreeable odor. In order 

 to study more closely the character of these secondary 

 amines, the platinum double salt and the acetyl and benzoyl 



1 Since these investigations were made, Soderbaum and Widman have obtained 

 Cymidin (Carvacrylamine) by another method. See Berichte der Deutschen 

 chem. Gesellschaft XXL, 2127. 



117 



