Sodium Hydroxide → HCID 54173080, compound

Participants

Reaction Steps

A mixture of (335 mg, 0.951 mmol, 1.0 eq) methyl, 3-[2-[3-(cyclopentyloxy)-4-methoxyphenyl]ethenyl]benzoate in 8 ml methanol and 1.9 ml (1.90 mmol, 2.0 eq) of 1N NaOH was heated to reflux for 1.5 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo, poured into 100 ml H2O, basified to pH 12, and washed once with ethyl acetate. The aqueous layer was acidified to pH 4 and extracted three times with ethyl acetate. The ethyl acetate extracts were combined, washed once with H2O, once with brine, dried over NA2SO4, and concentrated to yield 295 mg of white waxy crystals. Recrystallization from ethyl acetate-hexane afforded 100 mg, 34%/, of the cis isomer as white crystals. M.P.: 93°-94° C. Elemental Analysis: Calc'd for C21H22O4 : Calc'd: C, 74.53; H, 6.55. Found: C, 74.32; H, 6.68.

Provenance & Evidence