Hydrochloric Acid → Phenethyl (E)-caffeate

Participants

Reaction Steps

1 g of caffeic acid was dissolved in 25 mL of pyridine. 1.14 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 2.8 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 100 mL of 10% HCl and extracted with methylene chloride (2×50 mL). The combined organic extract was washed with water (2×50 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 120 mg and the purity was by TLC single spot.

Provenance & Evidence