Sodium Hydroxide → HCID 68875429, compound

HRID 1436007Notes

Reaction equation

HRID 1436007 reaction equation
C[O:2][C:3](=[O:15])[CH:4]=[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)[CH3:6].[OH-].[Na+]>O.CO.C1COCC1>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([C:5]([CH3:6])=[CH:4][C:3]([OH:15])=[O:2])[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68877312HCID 68877312, compound

Product 1

HCID 68875429HCID 68875429, compoundYield 65.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Methoxy-phenyl)-but-2-enoic acid methyl ester (2 g, 7.9 mmol) and sodium hydroxide (0.78 g, 19.4 mmol) were dissolved in a mixture of water (50 ml), methanol (50 ml) and THF (50 ml). The mixture was stirred at ambient temperature for 16 hours and then concentrated under reduced pressure. The remaining aqueous solution was diluted with water and extracted with EtOAc twice. The aqueous was collected and acidified to pH 4 and extracted with EtOAc three times. The organics were combined, dried (magnesium sulphate) and concentrated in vacuo to give 3-(3-Methoxy-phenyl)-but-2-enoic acid as a white crystalline solid (1 g, 55%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe remaining aqueous solution was diluted with water
  3. extractionextracted with EtOAc twice
  4. customThe aqueous was collected
  5. extractionextracted with EtOAc three times
  6. dry with materialdried (magnesium sulphate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-359ab89debcd40c0a7d075a7d3201c6b
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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