Carbon Dioxide → 1,3-Dihydroxy-2-naphthoic acid methyl ester

Participants

Reaction Steps

A mixture of 1,3-dihydroxynaphthalene (480 mg, 3.00 mmol) and potassium bicarbonate (750 mg, 7.5 mmol) in glycerol (1 mL) was heated under 1 atmosphere of CO2 to 115° C. for 5 hours then poured into 0.5M HCl (20 mL) and extracted with diethyl ether (3×5 mL). The combined ether layers were washed with brine (1×5 mL), dried (MgSO4) and filtered. This solution was then treated with a solution of diazomethane in diethyl ether until bubbling ceased. The ether was removed under reduced pressure and purified on silica gel eluting with 20% ethyl acetate/hexanes to provide (75 mg, 11%).

Provenance & Evidence