Water → 4-Methoxy-gamma-oxobenzenebutanoic acid

Participants

Reaction Steps

A solution of p-anisole (4.32 g, 50 mmol) and succinic anhydride (4.14 g, 40 mmol) were combined in 1,1,2,2-tetrachloroethane (10 mL) and nitrobenzene (40 mL) at 4° C. Aluminum chloride (24.56 g, 180 mmol) was then added gradually. The temperature was kept at 0°-5° C. and stirred overnight. Water was added and neutralized to quench the reaction. The aqueous phase was separated and washed with ether then reacidified and washed with ether again. The ether fractions were combined, dried and evaporated. The remaining residue was purified by flash silica chromatography to yield a white solid (7.55 g, 88%). 1H NMR (CDCl3) δ 7.98 (d, 3H), 6.88 (d, 2H), 3.76 (s, 3H), 3.30 (t, 2H), 2.76 (t, 2H).

Provenance & Evidence