5-(Benzyloxy)2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)phenol → 4-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol

Participants

Reaction Steps

A round bottomed flask was charged with 5-benzyloxy-2-(1,4-dioxaspiro[4.5]dec-7-en8-yl)phenol (6.90 g), ethanol (300 ml) and palladium (2.00 g, 10% on activated carbon). The reaction vessel was then evacuated and placed under a hydrogen atmosphere. This process was repeated 15 times before stirring vigorously for 64 hr under a hydrogen atmosphere. The reaction mixture was filtered through a celite plug, washing with ethyl acetate. The filtrate was concentrated in vacuo, furnishing the title compound (5.10 g, 100%) as a solid. δH (CD3OD) 1.65-1.87 (8H, m), 2.86-2.90 (1H, m), 3.90-4.06 (4H, m ), 6.27 (1H, dd), 6.29 (1H, d), 6.92 (1H, d); m/z(ES+) 251 (M+H+).

Provenance & Evidence