(+/-)-{4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetic acid → {4-[2,4-Dihydroxyphenyl]cyclohexylidene}acetic acid

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with (±)-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetic acid (25 mg), acidic Dowex resin (75 mg) and methanol (15 ml) then stirred at 60° C. for 3 hr. The reaction mixture was filtered through a celite plug, washing with methanol. The solvent was removed under reduced pressure to give an oil which was purified by preparative TLC (ethyl acetate/petroleum ether, 3:1, v/v), furnishing the title compound (6.5mg, 35%) as an oil. δH (CD3OD) 1.22-1.40 (2H, m), 1.90-2.10 (4H, m), 2.36-2.40 (2H, m), 3.08 (1H, tt), 5.62 (1H, s), 6.20 (1H, dd), 6.25 (1H, d), 6.84 (1H, d); m/z(ES+) 339 (M+H+).

Provenance & Evidence