Methyl Acrylate → HCID 19782730, compound

Participants

Reaction Conditions

Reaction Steps

To a four neck round bottom flask, equipped with a mechanical stirrer, a three-way stopcock, a thermometer and a reflux condenser connected to a cold trap and an oil bubbler, were charged, under nitrogen atmosphere and at room temperature, 45.8 g (0.22 moles) 2,6-di-t-butylphenol and 7.48 g (0.067 moles) potassium t-butoxide. The reaction mixture was heated to 165° C. and t-butanol was removed from the reaction mixture by nitrogen purging and collected in the cold trap. After approximately 10 minutes substantially all of the t-butanol had been removed, 6.4 ml (0.067 moles) N-methylpyrrolidinone were added and stirring continued. Next the reaction mixture, while stirring, was cooled down to 120° C. over a 5 minute period. Then 21 ml (0.23 moles) methyl acrylate were added all at once. The temperature dropped to 105° C. then rose to 139° C. in approximately 2 minutes. When the reaction was completed, the reaction mixture was cooled to about 90° C. and acidified with 4 ml of glacial acetic acid. Then the acidified mixture was diluted with a solution of 40 ml methanol and 8 ml water, allowed to cool to room temperature and the product was filtered. 64.6 g of methyl 3-(2,6-di-t-butyl-4-hydroxyphenyl)propionate was obtained.

Provenance & Evidence