4-Aminophenol → Ethyl 2-(4-aminophenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

4-amino phenol (500 mg, 4.58 mmol) was suspended in acetonitrile (60 mL), the mixture cooled to 0° C. and ethyl 2-bromoacetate (0.53 mL, 4.81 mmol) added. CsCO3 (1.9 g, 10 mmol) was added in portions and the mixture stirred for 16 h, allowing to warm to RT. The mixture was filtered, the residue washed with acetonitrile and the filtrate evaporated to dryness. The crude product was suspended in DCM (˜30 mL), filtered and this filtrate evaporated to dryness to afford ethyl 2-(4-aminophenoxy)acetate (860 mg) as a dark oil that solidified on standing. 1H NMR (400 MHz, CDCl3) δ 6.79-6.74 (m, 2H), 6.66-6.60 (m, 2H), 4.53 (s, 2H), 4.26 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H).

Provenance & Evidence