Formation of byproducts in the synthesis of (2,6-dimethylphenyl)-triphenylmethane

CHED 578

Kimberly Carrie Strohl and Dale Robert Powers, dpowers@elmira.edu. Division of Math and Natural Science, Elmira College, 1 Park Place, Elmira, NY 14901

The synthesis of (2,6-dimethylphenyl)-triphenylmethane (I) produces several products.  (Powers, Boeltz, and Drahl – 231st ACS National Meeting, 2006)   These byproducts were found to be produced during the reaction of (2,6-dimethylphenyl)-diphenylmethanol (V) with aniline hydrochloride.   These byproducts form by the way of a trityl cation in acidic conditions.  (Patai and Dayagi, J.Chem.Soc., 1962, 716-723).  Compounds I, II, III, IV are difficult to separate – but the separation of II and III from VI should be possible.  Progress was made in the purification (98+%) of (V).