Allyl Alcohol → Ethyl 4-(3-oxopropyl)benzoate

Participants

Reaction Steps

To a solution of 20 g (69.9 mmol) of ethyl 4-iodobenzoate, 0.47 g (2.1 mmol) of palladium acetate, 14.7 g (175 mmol) of sodium bicarbonate, and 22.5 g (70 mmol) of tetrabutylammonium bromide in 200 mL of dimethyl formamide were added, under nitrogen, 6.89 g (118.8 mmol) of allyl alcohol. The reaction mixture was stirred at room temperature for 42 hours. The dimethyl formamide was then removed by evaporation under reduced pressure and the residue was dissolved in 300 mL of ethyl acetate. This was washed with water (3×50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residual solid was purified by column chromatography on silica gel, eluting with 7:3 hexane:ethyl acetate to give 13.3 g (98%) of 3-(4-ethoxycarbonylphenyl)-1-propanal as a light yellow oil. 1H NMR (CDCl3) δ 10.02 (1H, s), 8.18 (2H, d, J=7.3 Hz), 7 47 (2H, d, J=7.3 Hz), 4.56 (2H, q, J=6.5 Hz), 3,21 (2H, t, J=6.5 Hz), 3.02 (2H, t, J=6.5 Hz), 1,59 (3H, t, J=6.5 Hz), Taylor, E. C. et al., J. Org. Chem., 57, 3218 (1992); J. Org. Chem., 60, 6684 (1995).

Provenance & Evidence