Water → Phenethyl (E)-caffeate

HRID 2221377Notes

Reaction equation

HRID 2221377 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>[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

6

Reactant 4

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

Product 1

HCID 5281787Phenethyl (E)-caffeate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

10.0 g of caffeic acid and 6.1 g potassium bicarbonate were mixed in 50 mL of dimethylsulfoxide. 7.6 mL of phenethyl bromide were added and the reaction mixture was heated to 70° C. under agitation. The mixture was stirred for 3 hrs, and then cooled to <25° C. The reaction mixture was slowly added to 500 mL of water under agitation to precipitate the product, which was recovered by filtration. The crude product was washed with dilute potassium bicarbonate and toluene and was then recrystallized via cooling from 200 mL boiling toluene to obtain caffeic acid phenethyl ester The yield was 9.0 g and the assay was 100%.

Workup

  1. temperaturecooled to <25° C
  2. customto precipitate the product, which
  3. filtrationwas recovered by filtration
  4. washThe crude product was washed with dilute potassium bicarbonate and toluene
  5. customwas then recrystallized
  6. temperaturevia cooling from 200 mL

Sources & evidence

ORD record
ord-43e0163e9170417fbfdc1e1597243f6d
Source dataset
uspto-grants-2008_05
Patent number
US07368593B1

Reaction notes

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