4'-Hydroxyacetophenone → Ethyl 2-(4-acetylphenoxy)acetate

Participants

Reaction Steps

To an ambient slurry of p-hydroxyacetophenone (20 g, 147 mmol) and K2CO3 (30.4 g, 220 mmol) in acetone (150 mL) was added ethyl bromoacetate (17.2 mL, 154 mmol). The slurry was stirred for 18 h and was quenched by the addition of H2O (150 mL) and Et2O (75 mL). The layers were separated, and the aqueous was extracted with additional Et2O (3×75 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give an oil that was used without further purification. MS (ESI) m/e 223 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.22 (t, J=7.12 Hz, 3H), 2.52 (s, 3H), 4.18 (q, J=7.12 Hz, 2H), 4.90 (s, 2H), 7.04 (m, 2H), 7.92 (m, 2H).

Provenance & Evidence