Water → Phenethyl (E)-caffeate

Participants

Reaction Steps

1 g of caffeic acid was dissolved in 25 mL of dimethylsulfoxide. 0.77 mL of 25% aqueous sodium hydroxide solution was added while stirring. Stirring continued for 1 hr. At the end of this period a solution of 1.10 mL of phenethyl bromide was added slowly in 30 minutes. The resulting reaction mixture was stirred at room temperature for 50 hrs. Next, the reaction mixture was poured into 75 mL of cold water and extracted with ethyl acetate (3×60 mL). The combined organic extract was washed with 50 mL of 5% HCl and water (60 mL). After drying over sodium sulfate, the solvent was distilled off under vacuum. The residue was crystallized from toluene by treatment with activated carbon to obtain caffeic acid phenethyl ester. The yield was 760 mg and the purity was greater than 90%.

Provenance & Evidence