Methylparaben → Methyl 4-(allyloxy)benzoate

Participants

Reaction Steps

The reaction mixture of 4-hydroxybenzoic acid, methyl ester (20.0 g, 131.0 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA), allyl bromide (17.0 g, 138.0 mmol) and potassium carbonate (45.0 g, 329.0 mmol) in DMSO (30.0 mL) was stirred at room temperature for 8 hours. EtOAc (150 mL) was added, and the organic layer was washed with water (30×3 mL) and then dried over MgSO4. After filtration, the solvent was removed. The product was used in the next step without further purification, (25.0 g, yield 99%). 1H NMR (400 MHz, CDCl3) δ ppm 7.91 (2H, m), 6.86 (2H, m), 5.98 (1H, dt, J=17.2, 5.3 Hz), 5.35 (1H, dd, J=17.2, 1.6 Hz), 5.24 (1H, dd, J=10.6, 1.6 Hz), 4.52 (2H, d, J=5.5 Hz), 3.81 (3H, s).

Provenance & Evidence