Ethanol → Benzeneacetic acid, 2,4-dihydroxy-alpha-oxo-, ethyl ester

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Reaction Steps

To a solution of resorcinol (5.0 g, 45.4 mmol, 1 eq) in diethyl ether (30 mL) was added 3M EtMgBr (18.5 mL, 50.0 mmol, 1.1 eq)) dropwise under argon. The reaction mixture was stirred at rt for 20 min. The ether was removed under vacuum and anhydrous toluene (80 mL) was added. A solution of oxalyl chloride (4.36 mL, 50 mmol, 1.1 eq) in toluene (20 mL) was added to the mixture dropwise under argon. The reaction mixture was stirred at rt for 15 h. Anhydrous ethanol (40 mL) was added to the mixture and the reaction mixture was stirred at rt for 1 h. Most of the solvent was evaporated and then EtOAc (60 mL) and water (40 mL) were added to the mixture. The layer was separated and the organic layer was washed with water (2×40 mL), dried over Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified by column chromatography eluted with 20% EtOAc/hexane then 50% EtOAc/hexane solution to afford white solid (5.88 g, 62%) as product. 1H-NMR (CD3CN): δ 7.62 (d, J=9.0 Hz, 1H), 6.50 (dd, J=2.3, 9.0 Hz, 1H), 6.41 (d. J=2.3 Hz, 1H), 4.44 (q, 2H), 1.40 (t, 3H).

Provenance & Evidence