Sodium Bicarbonate → Phenethyl (E)-caffeate

Participants

Reaction Conditions

Reaction Steps

1 g of caffeic acid was dissolved in 20 mL of ethanol and 2 mL water. 0.5 g of sodium bicarbonate was added while stirring. Stirring continued for 3 hr. Solvent and water were distilled off under vacuum. The residual solid was dissolved in 25 mL dimethylformamide and heated to 150° C. To this hot reaction mixture 0.8 mL of phenethyl bromide was added. The resulting reaction mixture was stirred for 40 hrs. Next, the reaction mixture was poured into 75 mL of cold water and extracted with ether (3×70 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 304 mg and the purity was greater than 90%.

Provenance & Evidence