Water → Phenethyl (E)-caffeate

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%.

1. stirringStirring
2. customThe resulting reaction mixture
3. stirringwas stirred at room temperature for 50 hrs
4. extractionextracted with ethyl acetate (3×60 mL)
5. extractionThe combined organic extract
6. washwas washed with 50 mL of 5% HCl and water (60 mL)
7. dry with materialAfter drying over sodium sulfate
8. distillationthe solvent was distilled off under vacuum
9. customThe residue was crystallized from toluene by treatment with activated carbon

ORD record

ord-bddf4e597ade47c594a2f05c60e52aa9

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07368593B1