Methyl Acrylate → HCID 19784855, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 25.0 grams (52.7 mmol) of bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, 10.0 grams of magnesium sulfate, 100 mg of 5% palladium on carbon, and 200 ml of tetrahydrofuran is hydrogenated (50 psi, ambient temperature) on a Parr apparatus. Solids are removed by filtration. The filtrate is cooled to 10° C. (under nitrogen atmosphere) and treated with 0.6 gram (5.3 mmol) of potassium tert-butoxide. Methyl acrylate (45.5 grams, 527 mmol) is added to the reaction mixture over a five-minute period. The reaction mixture is then stirred at ambient temperature for two hours, treated with another portion of 0.6 gram of potassium tert-butoxide and stirred overnight at ambient temperature. The reactions mixture is diluted with ether (300 ml), washed with 1N hydrochloric acid (2×200 ml), washed with saturated sodium bicarbonate solution (200 ml), dried over anhydrous magnesium sulfite and concentrated to an oil. The oil is purified by flash chromatography (silica gel; 4:1 hexane: ethyl acetate) to yield a solid which is recrystallized from methanol to afford 8.8 grams (26% yield) of the title compound as a white solid melting at 117°-118° C.

Provenance & Evidence