Allyl bromide → Methyl 5-formyl-2-(1-prop-2-enyloxy)benzoate

Participants

Reaction Steps

Methyl 5-formylsalicylate (3.3 g, 18 mmol), allyl bromide (1.7 mL, 20 mmol), and potassium carbonate (2.8 g, 20 mmol) were stirred at room temperature in DMF (20 mL) overnight. After concentration, the mixture was diluted with EtOAc and extracted with water (5×), then brine. After drying (MgSO4), solvent was removed to give a yellow solid (4.2 g). 1H-NMR(300 MHz, CDCl3): 9.92 (s, 1H), 8.35 (d, 1H, J=2 Hz), 8.00 (dd, 1H, J=9,2 Hz), 7.09 (d, 1H, J=9 Hz), 6.13-6.01 (m, 1H), 5.58-5.34 (m, 2H), 4.75-4.73 (m, 2H), 3.93 (s, 3H). Anal. Calc'd for C12H12O4 : C, 65.45; H, 5.49; Found: C, 65.10; H, 5.36.

Provenance & Evidence