Hydrochloric Acid → Ethyl 3-methyl-4-hydroxy-5-ethylbenzofuran-2-carboxylate

Participants

Reaction Steps

To a solution of 1.92 g (7.22 mmol) of ethyl (2-acetyl-4-ethyl-3-hydroxyphenoxy)acetate in 35 mL of absolute ethanol was added 0.54 g (7.94 mmol) of sodium ethoxide. The reaction was heated at reflux for 3 h and then cooled to room temperature, acidified with 1N HCl, and concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/heaxnes (1:9) to provide 0.9 g of ethyl 3-methyl-4-hydroxy-5-ethylbenzofuran-2-carboxylate.

Provenance & Evidence