4-Aminophenol → 1-(4-hydroxyphenyl)pyrrolidin-2-one

Participants

Reaction Steps

To a solution of p-aminophenol (0.545 g, 5.00 mmol) in dry MeCN (5 mL) at 0° C. was added K2CO3 (1.38 g, 10.0 mmol), followed by dropwise addition of 4-chlorobutanoyl chloride (0.56 mL, 5.0 mmol). The mixture was stirred at rt for 40 min and then brought to reflux. Dry DMF (5 mL) was added after 90 min and heating was continued for an additional 2 h. The mixture was cooled, poured into water, and extracted with EtOAc (×8). Combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.171 g of the title compound as a colorless solid: MS (APCI) m/z 177 (M+).

Provenance & Evidence