Potassium Hydroxide → O-Coumaric Acid

HRID 655069Notes

Reaction equation

HRID 655069 reaction equation
C([O:3][C:4](=[O:14])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])C.[OH-].[K+]>C(O)C.O>[OH:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1/[CH:6]=[CH:5]/[C:4]([OH:14])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 576496Ethyl 3-(2-hydroxyphenyl)prop-2-enoate

Product 1

HCID 637540O-Coumaric AcidYield 51.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 100.0 g 3-(2-hydroxy-phenyl)-acrylic acid ethyl ester in 500 ml of ethanol, a solution of 50.9 g potassium hydroxide in 500 ml of water was dropped in at room temperature. After stirring at reflux for 28 hours, the reaction mixture was concentrated. The residue was diluted with 500 ml HCl 2N and extracted with ether. The organic phase was washed with 2N HCl and water, dried and evaporated to dryness. The resulting solid was recrystallized to yield 44.3 g of colourless crystals.

Workup

  1. temperatureat reflux for 28 hours
  2. concentrationthe reaction mixture was concentrated
  3. additionThe residue was diluted with 500 ml HCl 2N
  4. extractionextracted with ether
  5. washThe organic phase was washed with 2N HCl and water
  6. customdried
  7. customevaporated to dryness
  8. customThe resulting solid was recrystallized

Sources & evidence

ORD record
ord-c69e671eabb14e97a6afaf4458a2d516
Source dataset
uspto-grants-2011_12
Patent number
USRE043006E1

Reaction notes

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