(+/-)-{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 equipped with magnetic stirrer was loaded with (±)-{4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetic acid (25 mg, 74 mmol), 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 a yellow oil (15 mg) which was purified by preparative TLC (ethyl acetate/petroleum ether, 3:1, v/v), furnishing the title compound (6.5 mg, 35%) as an oil. m/z (ES+) 339 (M+H+).

Provenance & Evidence