Toluene → [4-(3-Aminophenoxy)phenyl][4-(phenylethynyl)phenyl]methanone

Participants

Reaction Conditions

Reaction Steps

In a 500 mL flask equipped with nitrogen inlet, overhead stirring assembly, Dean-Stark trap, and reflux condenser were placed 3-aminophenol (18.5 g, 0.17 mol), 4-phenylethynyl-4'-fluorobenzophenone (43.2 g, 0.14 mol), potassium carbonate (22 g, 0.16 mol), toluene (30 mL), and DMAc (200 mL). The mixture was heated to 142° C. for 8 h, then cooled to room temperature. The reaction mixture was poured into water and the resulting light yellow powder was collected by filtration. Recrystallization from water/acetone (50/50) (v) and sodium dithionite (0.5 g) afforded 51.8 g (95% yield) of the desired product: m.p. 137°-139° C. IR (KBr); 3414 and 3342 cm-1 (NH2); 3040, 1596, and 1499 cm-1 (aromatic C--H); 2216 cm-1 (C≡C), and 1646 cm-1 (C=O): Mass Spec. m/e (relative intensity): M+, 389.4 (100); FW=389.44 g/mol.

Provenance & Evidence