6-(3-Hydroxyphenyl)-3,4-dihydronaphthalene-1(2H)-one → 6-(3-Hydroxyphenyl)-1-naphthol

Participants

Reaction Steps

6-(3-Hydroxyphenyl)-3,4-dihydronaphthalene-1(2H)-one (503 mg, 2.11 mmol, 1 eq) and Pd/C (505 mg) are suspended in p-cymene (15 ml). The reaction mixture is refluxed for 6 h, cooled, filtered over Celite and extracted with 1 M NaOH. The aqueous phase is acidified with 1 M HCl and extracted with ether. The combined organic phases are washed with water, dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. Purification by column chromatography with dichloromethane/ethyl acetate 9/1 as the eluent yields the desired product in a yield of 16%, 83 mg.

Provenance & Evidence