4-Nitrobenzoic Acid → Methyl [6-(4-nitrobenzoyl)-2H-1,3-benzodioxol-5-yl]acetate

Participants

Reaction Steps

To a solution of methyl 3,4-methylenedioxyphenylacetate (5.4 g, 28 mmol) in ClCH2CH2Cl (100 mL) was added 4-nitrobenzoic acid (7.2 g, 43 mmol) and P2O5 (18 g) at room temperature under argon. The mixture was refluxed for 28 h, cooled to room temperature, then cold water was added slowly. The resulting mixture was carefully neutralized with solid K2CO3, and extracted with 1:1 hexane/EtOAc (2×300 mL). The combined extracts were washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was separated by chromatography (3:1 hexane/EtOAc) to afford the title compound as a yellow solid (4.7 g, 14 mmol, 50%). 1H NMR (CDCl3) 8.32 (d, 2H, J=8.5), 7.92 (d, 2H, J=8.5), 6.85 (s, 1H), 6.81 (s, 1H), 6.07 (s, 2H), 3.88 (s, 2H), 3.63 (s, 3H).

Provenance & Evidence