Sodium Carbonate → Phenyl 4-[2-(2-methoxyethoxy)ethoxy]benzoate

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Reaction Steps

To a solution of phenyl 4-hydroxybenzoate (2.1 g, 9.8 mmol) in tetrahydrofuran (40 mL) was added a 60% suspension of sodium hydride in mineral oil (408 mg, 10.2 mmol) and the mixture was stirred at room temperature for about 30 minutes. Then 1-bromo-2-(2-methoxyethoxy)ethane (2.5 g, 13.7 mmol) was added and stirring was continued for about 5 days. The mixture was poured into saturated aqueous sodium carbonate and was extracted with ethyl acetate, the combined organic extracts were washed with saturated aqueous sodium carbonate, dried (Na2SO4), filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (10:1) as eluent to provide the desired product. 1H NMR (500 MHz, CDCl3) δ 3.40 (s, 3H), 3.60 (m, 2H), 3.76 (m, 2H), 3.92 (t, J=8 Hz, 2H), 4.22 (t, J=8 Hz, 2H), 7.00 (d, J=8 Hz, 2H), 7.22 (m, 3H), 7.42 (d, J=8 Hz, 2H), 8.17 (d, J=8 Hz, 2H).

Provenance & Evidence