Water → (+/-)-6-[2-(1,2-Epoxy-2,6,6-trimethylcyclohexanyl)ethynyl]naphthoic acid

Participants

Reaction Steps

To a suspension of 0.135 g (0.218 mmol) of 80% magnesium monoperoxyphthalate acid (MMPP) and 2 ml iso-propyl alcohol was added enough water (0.20 ml) to just dissolve the solid. This solution was added to a solution of 0.058 g (0.182 mmol) of 6-[2-(2,6,6-trimethylcyclohex-1-enyl)ethynyl]-2-naphthoic acid (Compound 4) in 1 ml iso-propyl alcohol and stirred at ambient temperature for 3 days. The solution was treated with 2 ml of brine and extracted with 3×10 ml ethyl acetate. The organic extracts were combined and washed with 5 ml saturated aqueous NaCl and dried (MgSO4). The solvent was removed in-vacuo and the residue purified by flash chromatography (SiO2, 75:25 ethyl acetate in hexanes) to give the title compound as a white solid

Provenance & Evidence