Ethanol → 4-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol

Participants

Reaction Steps

A round bottomed flask equipped with magnetic stirrer was charged with 5-(benzyloxy)-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)phenol (14.5 g, 42.8 mmol) and tetrahydrofuran (50 ml). The stirred mixture was gently heated until a solution formed, after which the solution was allowed to cool to room temperature. Ethanol (100 ml) and palladium (4.54 g, 10% on activated carbon) were added sequentially. The reaction vessel was then evacuated, placed under a hydrogen atmosphere and stirred vigorously for 24 hr. The reaction mixture was filtered through a celite plug, washing with ethyl acetate. The filtrate was concentrated in vacuo to give an off white solid. The crude solid was slurried in dichloromethane (200 ml), then collected on a sinter, affording the title compound (10.2 g, 95%) as a white solid. m/z(ES+)251(M+H+).

Provenance & Evidence