3-Methoxyphenol → 7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methoxyphenol (5.00 g, 40.3 mmol) and 3,3-dimethylacrylic acid (4.03 g, 40.3 mmol) were ground in a mortar. The mixture was then added portion-wise into polyphosphoric acid (8 g) at 90° C. After stirring at 90° C. for 30 min, the reaction mixture was quenched with ice, then extracted with diethyl ether. The organic layers were washed with water; brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo and purified by column chromatography (silica gel, 10% ethyl acetate in hexane) to give the title compound as a yellow solid.

Provenance & Evidence