Water → N-(4-Methoxyphenyl)Acetamide

Participants

Reaction Steps

To an ice-cold solution of p-anisidine (25 g, 203.0 mmol) in DCM (300.0 mL) was added triethyl amine (90.0 mL, 609.0 mmol) dropwise and the reaction mixture was stirred at the same temperature for 15 min. Acetyl chloride (23.0 mL, 304.50 mmol) was then added and the reaction mixture was continued to stir at room temperature for 1 h. After the completion of the reaction (TLC monitoring), water (500 mL) was added and extracted with DCM (2×300 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product (30.0 g, 90%). 1H NMR (400 MHz, DMSO-d6): δ 1.99 (s, 3H), 3.70 (s, 3H), 6.86 (d, J=8.80 Hz, 2H), 7.48 (d, J=8.80 Hz, 2H) and 9.77 (br s, 1H).

Provenance & Evidence