Methyl 2-hydroxy-1-naphthoate → Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate

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Reaction Steps

Under an atmosphere of nitrogen, platinum oxide (5 g) was added to a solution of 2-hydroxy-naphthalene-1-carboxylic acid methyl ester (10 g) in acetic acid (200 mL). The nitrogen atmosphere was replaced by hydrogen, the pressure was increased to 4 bar and the mixture was stirred overnight. The resulting suspension was filtered and the filtrate was concentrated under vacuum to give an oil. The residue was purified by chromatography on silica, eluting with DCM. The fractions containing the desired product were combined and evaporated under vacuum to give the title compound as a colorless oil (11.7 g).

Provenance & Evidence