Potassium Hydroxide → O-Coumaric Acid

HRID 1870576

Reaction equation

HRID 1870576 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-d15b5863f9d84dc9ac9ba57a6513e3e7
Source dataset
uspto-grants-2000_08
Patent number
US06096918

Linked notes

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