(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclopentanone → (+/-)-3-(2,4-Dihydroxyphenyl)cyclopentanone

Participants

Reaction Steps

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclopentanone (8 mg) was heated at 50° C. in MeOH (3 ml) containing acidic ion exchange resin (0.1 g) for 3 hr. The reaction mixture was filtered and the resin washed with ethyl acetate (20 ml). The filtrate was concentrated in vacuo and the residue purified by flash column chromatography (SiO2, ethyl acetate) to furnish the title compound as a white solid (3.8 mg, 70%). δH (d4-MeOH) 2.52-2.13 (1H, m), 2.26-2.48 (4H, overlapping m), 2.53-2.60 (1H, m), 3.55-3.61 (1H, m), 6.29 (1H, dd), 6.33 (1H, d), 6.96 (1H, d); m/z (ES−) 251 ((M+60)−1)−.

Provenance & Evidence