Benzoic acid, 3,5-dihydroxy-, ethyl ester → Ethyl 3-hydroxy-5-oxo-3-cyclohexene-1-carboxylate

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Reaction Steps

3,5-Dihydroxybenzoic acid ethyl ester (10 g, 54.89 mmol) was dissolved in ethanol (15 mL), followed by adding sodium formate (4.48 g, 65.87 mmol), replacing inside a reactor with nitrogen at 30° C. for 15 minutes, adding palladium on carbon (364 mg) and reacting at 30° C. for 3 hours then at 40° C. over night. Catalyst was filtered off, followed by neutralization with a 1N HCl solution, concentration under reduced pressure and purification of thus obtained residue with silica gel column chromatography (hexane/ethyl acetate=1/1 to 0/1) to obtain an objective compound (1.53 g, 15.1%).

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