Hydrochloric Acid → Phenethyl (E)-caffeate

HRID 2221374Notes

Reaction equation

HRID 2221374 reaction equation
[C:1]([OH:13])(=[O:12])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1.[OH-].[Na+].[CH2:16](Br)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>N1C=CC=CC=1>[CH2:16]([O:12][C:1](=[O:13])/[CH:2]=[CH:3]/[C:4]1[CH:11]=[CH:10][C:8]([OH:9])=[C:6]([OH:7])[CH:5]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7666Phenethyl bromideHCID 14798Sodium HydroxideHCID 689043Caffeic Acid

Product 1

HCID 5281787Phenethyl (E)-caffeate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  1. stirringStirring
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature for 50 hrs
  4. extractionextracted with methylene chloride (2×50 mL)
  5. extractionThe combined organic extract
  6. washwas washed with water (2×50 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

Sources & evidence

ORD record
ord-794bd8804d664895bde65c3026b4a411
Source dataset
uspto-grants-2008_05
Patent number
US07368593B1

Reaction notes

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