4-Coumaric acid → Methyl p-coumarate

HRID 131268

Reaction equation

HRID 131268 reaction equation
S(Cl)(Cl)=O.[CH3:5]O.[OH:7][C:8]1[CH:18]=[CH:17][C:11]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1>C(OCC)(=O)C.CCCCCC>[OH:7][C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[CH:13][C:14]([O:16][CH3:5])=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 3224-Coumaric acidHCID 887MethanolHCID 24386Thionyl Chloride

Product 1

HCID 92203Methyl p-coumarateYield 88%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Thionyl chloride (1.33 mL) is added dropwise to methanol (30 mL) under ice-cooling and the solution is stirred for 10 minutes. To the solution is added 4-hydroxycinnamic acid (3.0 g) and the mixture is stirred at room temperature for 4 days. The reaction mixture is concentrated and the residue is diluted with ethyl acetate (50 mL), washed successively with a saturated sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is re-crystallized from ethyl acetate/n-hexane to methyl 4-hydroxycinnamate (2.86 g, yield; 88%) as pale yellow crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 4 days
  3. concentrationThe reaction mixture is concentrated
  4. additionthe residue is diluted with ethyl acetate (50 mL)
  5. washwashed successively with a saturated sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f67b979c4944e82b642e404992cee2e
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Linked notes

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