Phenol → 4-Phenoxy-4'-phenylethynylbenzophenone

Participants

Reaction Conditions

Reaction Steps

A 100 mL flask equipped with nitrogen inlet, overhead stirring assembly, Dean-Stark trap, and reflux condenser was charged with phenol (0.35 g, 0.0038 mol), 4-fluoro-4'-phenylethynylbenzophenone (0.10 g, 0.0038 mol) potassium carbonate (0.39 g, 0.003 mol), 25 mL of toluene, and 50 mL of DMAc. The mixture was heated to reflux and water was removed by azeotropic distillation, followed by the removal of toluene over a 20 hour period. The reaction was cooled to 23° C., and the mixture was poured into 1 L of acidic (HCl) water. The precipitate was collected by filtration to afford 1.37 g (96%) of 4-phenoxy-4'-phenylethynylbenzophenone as a white powder: mp 165.5° C. IR (KBr): 2216 cm-1 (ethynyl), 1650 cm-1 (carbonyl): 1H-NMR (CDCl3): 7.8-6.8 pp, (m H aromatic). Anal Calcd. for C27H18O2 : %C=86.61, %H=4.85. Found: %C=86.46, %H=4.68. The structure of this compound is given below: ##STR10## The DSC thermogram of this compound is presented in FIG. 3.

Provenance & Evidence