Pyridine → 2-(Dimethoxymethyl)-2-methylchroman-4-one

Participants

Reaction Steps

In 250 ml of toluene were dissolved 30 g (0.22 mmole) of 2-hydroxy acetophenone and 33.8(0.29 mmole) of pyruvic aldehyde dimethyl acetal; and, 6.3 ml (0.09 mmole) of pyridine was added thereto. After stirring at room temperature 30 minutes, the reactants were heated to reflux for 5 hours using Dean-Stark apparatus. The solvent was removed under reduced pressure and 100 ml of 2N HCl aqueous solution was added. The resultant solution was stirred for 1 hour at room temperature, extracted with ethyl acetate (20 ml×2), washed with 100 ml of water and then with 50 ml of saturated sodium chloride aqueous solution and purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (4:1) to obtain 39 g (0.16 mmole, yield 75%) of the title compound as a white solid.

Provenance & Evidence