Sulfuric Acid → Methyl 4-(4-fluorophenyl)-4-oxobutanoate

Participants

Reaction Steps

To a solution of 3-(4-fluorobenzoyl)-propionic acid (1.98 g, 10.0 mmol) in methanol (25 mL) was added 0.5 mL of conc. sulfuric acid. The resulting solution was stirred at room temperature under argon for 2 hours. The reaction mixture was neutralized with saturated sodium bicarbonate, the methanol was removed via rotary evaporator and the residue was dissolved in 50 mL of ethyl acetate. The resulting solution was washed with saturated sodium bicarbonate (3×50 mL) and brine (50 mL), dried over sodium sulfate and the solvent was removed in vacuo to give Methyl 3-(4-fluorobenzoyl)-propionate (2 g, 94%). IR (film) 3448, 3111, 3076, 3003, 3958, 1734, 1678, 1601, 1423, 1300, 1240, 1155, 1099 cm-1 ; 1H-NMR (CDCl3) δ 7.97 (2H, dd, J=9.0, 5.5 Hz), 7.10 (2H, t, J=8.9 Hz), 3.67 (3H, s) , 3.25 (2H, t, J=6.6 Hz), 2.73 (2H, t, J=6.6 Hz); 13C-NMR (CDCl3) δ 196.50, 173.34, 167.54, 164.17, 132.98, 130.77, 115.91, 115.62, 51.91, 33.31, 28.00.

Provenance & Evidence