Phenol → 4-Phenoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-fluorobenzaldehyde (5 g, 40.28 mmol) and phenol (3.8 g, 44.42 mmol) in DMF (50 mL) was added K2CO3 (11.13 g, 80.57 mmol) and the resulting mixture was stirred at 110° C. overnight. The mixture was filtered, the filtrate was diluted with cold water and the product was extracted with EtOAc. The organic layer was washed with 5% aqueous NaOH solution, saturated brine solution and dried over sodium sulphate. The organic layer was then concentrated under reduced pressure to afford 7.7 g (96.5% yield) of 4-phenoxy benzaldehyde as a pale brown oil. 1H NMR: (CDCl3) δ 9.9 (s, 1H), 7.8 (d, 2H), 7.4 (t, 2H), 7.2 (t, 1H), 7.0 (t, 4H).

Provenance & Evidence