The Synthesis of 2-Indenylphenols: Potential Ligands For Transition Metals

Author

Yoon Jae Kim, Eastern Illinois University

Degree Name

Master of Science (MS)

Semester of Degree Completion

2001

Thesis Director

Robert W. Chesnut

Abstract

The syntheses of 2-(2-indenyl)-phenol and 2-(1-indenyl)-phenol via a three-step sequence have been developed. In the first steps of the sequence, a Grignard reagent formed from 2-iodoanisole or 2-bromoanisole reacted with 1-indanone or 2-indanone in yields that ranged from 11.3% to 67.2%. The second step consisted of acid-catalyzed dehydration of the alcohol formed in step 1 to make a 2-inenyl anisole; yields in the second step were 45.2% to nearly quantitative. Finally, demethylation of the 2-indenyl anisole was achieved with AlBr₃ in ethanethiol in yields ranging from 52.9% to 0 %. Each product was characterized by ¹H and ¹³C NMR. The three products in the series leading to 2-(2-indenyl) phenol were also characterized by elemental analysis. Only the 2-(2-hydroxy-2-indenyl) anisole product was pure.

Recommended Citation

Kim, Yoon Jae, "The Synthesis of 2-Indenylphenols: Potential Ligands For Transition Metals" (2001). Masters Theses. 1580.
https://thekeep.eiu.edu/theses/1580