Benzoyl chloride → Methyl 2-(2-Benzoyl-4,5-methylenedioxyphenyl)propionate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(3,4-methylenedioxyphenyl)propionate (1.04 g, 5 mmol) in CH2Cl2 (30 mL) at 0° C. was added SnCl4 (1M solution in CH2Cl2, 9 mL, 9 mmol). Then a solution of benzoyl chloride (1 mL) in CH2Cl2 (10 mL) was added dropwise and the mixture obtained was warmed to 25° C. for 20 h with stirring. The reaction mixture was poured into a separatory funnel containing Na2CO3 solution (sat. 50 mL) and some ice. The organic layer was separated and the aqueous was extracted with CH2Cl2 (3×50 mL). The combined extracts were washed with water (50 mL), NaHCO3 (sat. 40 mL) and brine (50 mL) and dried over Na2SO4. The pure product (360 mg, 23%) was obtained by chromatography on silica gel (hexane/ethyl acetate=4:1). 1H NMR (CDCl3) 7.80-7.45 (m, 5H), 6.96 (s, 1H), 6.79 (s, 1H), 6.03 (s, 2H) 3.70 (m, 1H), 3.58 (s, 3H), 1.47 (d, J=7.4, 3H).

Provenance & Evidence