Water → Phenethyl (E)-caffeate

HRID 2221378Notes

Reaction equation

HRID 2221378 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.C(=O)(O)[O-].[K+].[CH2:19](Br)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CS(C)=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[CH2:19]([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)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7666Phenethyl bromideHCID 516893Potassium BicarbonateHCID 689043Caffeic Acid

Product 1

HCID 5281787Phenethyl (E)-caffeate

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

1.0 g of caffeic acid was dissolved in 5 mL of dimethylsulfoxide and 0.55 g potassium bicarbonate were added and the mixture was allowed to react for 2 hours at room temperature. 0.75 mL of phenethyl bromide and 0.07 g of benzyl tributyl ammonium chloride were added and the reaction mixture was stirred for 90 hours. The reaction mixture was slowly added to 50 mL of water under agitation to precipitate the product, which was recovered by filtration. The crude product was then recrystallized from 17.5 mL boiling toluene to obtain caffeic acid phenethyl ester The yield was 830 mg and the purity was 97%.

Workup

  1. customto react for 2 hours at room temperature
  2. customto precipitate the product, which
  3. filtrationwas recovered by filtration
  4. customThe crude product was then recrystallized from 17.5 mL

Sources & evidence

ORD record
ord-db3ae09ff17341969718637ba5c43513
Source dataset
uspto-grants-2008_05
Patent number
US07368593B1

Reaction notes

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