Water → tert-Butyl 3-(4-hydroxyphenyl)prop-2-enoate

Participants

Reaction Conditions

Reaction Steps

4-Bromophenol (30.0 g), 33.5 g of tert-butyl acrylate, 50 mg of palladium acetate, and 27.9 g of potassium carbonate were dissolved in 300 mL of N-methylpyrrolidone, followed by stirring at 120° C. for 3 hours. The reaction solution was cooled to room temperature and 900 mL of water and 300 mL of dichloromethane were added thereto. The organic layer was separated and the water layer was extracted with 100 mL of dichloromethane twice. The organic layer was collected, washed with a 10% hydrochloric acid, saturated sodium bicarbonate water, and saturated saline, and dried by adding sodium sulfate. Sodium sulfate was removed and the mixture was purified by column chromatography (alumina/silica gel, dichloromethane), and the solvent was distilled away under a reduced pressure. As a result, tert-butyl 4-hydroxycinnamate (51 g) was obtained as a white solid.

Provenance & Evidence