Benzoyl chloride → 1,3-Benzodioxole-5-acetic acid, 6-benzoyl-, methyl ester

Participants

Reaction Steps

To a solution of methyl 3,4-methylenedioxyphenylacetate (150 mg, 0.77 mmol) in CH2Cl2 (5 mL) was added SnCl4 (1.0M solution in CH2Cl2 ; 1.5 mL, 1.5 mmol) at 0° C. Then benzoyl chloride (130 μL, 1.1 mmol) was added. The reaction mixture was allowed to warm slowly to room temperature. After 24 h, the mixture was added to a saturated NaHCO3 solution (30 mL), diluted with 1:1 hexane/EtOAc (60 mL), washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was separated by chromatography on silica gel (4:1 hexane/EtOAc) to yield the title compound (110 mg, 48%). 1H NMR (CDCl3) 7.78-7.45 (m, 5H), 6.88 (s, 1H), 6.84 (s, 1H), 6.04 (s, 2H), 3.80 (s, 2H), 3.61 (s, 3H).

Provenance & Evidence