Potassium Carbonate → Ethyl 2-[2-(t-butyloxy)-2-oxo-ethoxy]-5-formylbenzoate

Participants

Reaction Steps

Phenol 2c (1.0 g, 5.2 mmol), t-butyl bromoacetate (0.84 mL, 5.2 mmol), and potassium carbonate (0.79 g, 5.7 mmol) were heated at 65° C. in DMF (8 mL) overnight. After solvent removal, the mixture was diluted with EtOAc and extracted with water (3×), then brine. Drying (MgSO4) and removal of solvent gave a clear yellow oil (1.56 g). 1H-NMR(300 MHz, CDCl3): 9.93 (s, 1H), 8.35 (d, 1H, J=2 Hz), 7.99 (dd, 1H, J=9,2 Hz), 6.95 (d, 1H, J=9 Hz), 4.71 (s, 2H), 4.41 (q, 2H, J=7 Hz), 1.48 (t, 3H, J=7 Hz). Anal. Calc'd for C16H20O6 : C, 62.33; H, 6.54; Found: C, 62.05; H, 6.58.

Provenance & Evidence