4-Coumaric acid → Methyl-P-Coumarate

HRID 2117032Notes

Reaction equation

HRID 2117032 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[N+](=[CH2:15])=[N-]>CCOC(C)=O.CCOCC>[CH3:15][O:9][C:8](=[O:10])/[CH:7]=[CH:6]/[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 3224-Coumaric acidHCID 9550Diazomethane

Product 1

HCID 5319562Methyl-P-Coumarate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxycinnamic acid (0.407 g, 2.48 mmol) in EtOAc, a solution of diazomethane in Et2O was added until the yellow color persisted. Excess diazomethane was quenched by the addition of AcOH and the reaction mixture was evaporated to dryness. The residue was dissolved in EtOAc and washed with 10% aqueous HCl, saturated NaHCO3 and brine. The organic layer was dried over anhydrous MgSO4 and evaporated to dryness. The residue was purified by flash column chromatography, using a gradient from 10%-20% EtOAc in hexane, to give E-3-(4-hydroxyphenyl)acrylic acid methyl ester as a white solid (0.362 g).

Workup

  1. customExcess diazomethane was quenched by the addition of AcOH
  2. customthe reaction mixture was evaporated to dryness
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 10% aqueous HCl, saturated NaHCO3 and brine
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-8e2cc87c2aa54007a3c0fda5f915d07f
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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