Methyl Acrylate → HCID 19834309, compound

Participants

Reaction Conditions

Reaction Steps

Methyl acrylate (64.9 grams, 750 mmol) is rapidly added under a nitrogen atmosphere to a mixture of 16.9 grams (38 mmol) of alpha,alpha'-bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-p-xylene, 0.85 gram of potassium tert-butoxide and 70 ml of tetrahydrofuran. The reaction is exothermic and the temperature exceeds 40° C. for one hour. The reaction mixture is then heated at 60° C. for four hours and allowed to stand overnight at ambient temperature. The reaction mixture is diluted with ether (300 ml), washed consecutively with saturated sodium bicarbonate solution (200 ml), water (4×500 ml), and saturated sodium chloride solution (200 ml), dried over anhydrous magnesium sulfate and evaporated to an oil. The oil is stirred with methanol and a precipitate forms. The supernatant liquid is concentrated to give a solid which is purified by flash chromatography (silica gel; 9:1 hexane:ethyl acetate) to afford 4.6 grams (20% yield) of the title compound as a white solid melting at 84°-85° C.

Provenance & Evidence