Acetone → 2,2-Dimethyl-4-oxo-4H-benzo[d][1,3]dioxine-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-formylsalicylic acid (Aldrich, 4.12 g, 24.8 mmol) in TFA (30 ml), TFAA (10 ml) and acetone (10 ml) was heated at 90° C. overnight. The reaction mixture was concentrated under reduced pressure. The residual oil was taken up in EtOAc and washed with a saturated aqueous solution of NaHCO3 and brine. The organic layer was dried- over MgSO4 and the solvent was removed under reduces pressure. The crude product was purified by flash chromatography on silicagel (EtOAc/c-Hex (80/20)) to give 1.8 g (35%) of the title compound as a white powder. 1H NMR (CDCl3) δ: 1.80 (s, 6H), 7.09 (d, J=8.7 Hz, 1H), 8.09 (dd, J=8.7, 2.3 Hz, 1H), 8.45 (d, J=1.9 Hz, 1H).

Provenance & Evidence