12 



(or also a methoxyl-group in the a-position) would under certain con- 

 ditions enter into the nucleus: 



HBr 



CPLOf \cHBr.CHBr.CH,-> CH 3 0{ >: CH . CHBr . CH r 



During the further formation of the ketone dibrominated in the nucleus, 



Br H 



CH Q Of \CO.CHBr.CK 



Br H 



Hoering of course assumes a migration of the bromine atom entered 

 in double, into the ortho-position towards the methoxyl-group, and 

 supports this view by similar observations made by Z in eke in the 

 case of bromine additions in the eugenol series. Dibromanethol di- 

 bromide, w r hose abnormal behaviour also appeared in its indifference 

 towards alcohol, yielded with sodium methylate, — contrary to the 

 other dibromides — bromopropenyldibromanisol 



/^ 

 C 6 H 2 ^-OCH 3 



^CH:CBr.CH 3 



of the melting point 5 8°. This body is not changed by bromine, 

 but in the presence of hydrobromic acid as catalyser it absorbs at- 

 mospheric oxygen, and is converted with strong symptoms of luminiscence 

 into a brominated ketone 



/^ 



C 6 H,^-OCH g 



^CO.CHBr.CH 3 



of the melting point 101 . 



In an experiment to substitute in monobromanisyl-bromoethyl ketone the 

 bromine atom in the side-position by OH, O • COCH 3 , or O • COC 6 H 5 , 

 Hoering only obtained the two esters, but not the keto alcohol itself. 

 He further obtained, as a by-product of the preparation of the tetra- 

 brominated anethol (by dropping liquid anethol on bromine), in con- 

 sequence of the splitting-up of the methoxyl-group by the hydrobromic 

 acid generated, a tetrabrominated pseudo-phenol, which could also be 

 produced from the tetrabromanethol itself by the action of the hydro- 

 bromic and glacial acetic acids. When this pseudo-phenol was boiled 

 with glacial acetic acid and lead acetate, one of the bromine atoms in 

 the side-position was substituted by acetyl. 



