Water → 2-Propenoic acid, 3-(4-fluorophenyl)-, methyl ester

HRID 1272267Notes

Reaction equation

HRID 1272267 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.CI.[C:15](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10]([O:12][CH3:15])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 980703-(4-Fluorophenyl)-2-propenoic acid

Product 1

HCID 9587502-Propenoic acid, 3-(4-fluorophenyl)-, methyl esterYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-fluorophenyl)-2-propenoic acid (24.2 g, 146 mmol) in DMF (120 ml) were added methyl iodide (31.1 g, 219 mmol) and potassium carbonate (40.4 g, 292 mmol) at room temperature and the mixture was stirred for 72 hours. The resulting mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane to obtain 24.5 g (yield 93%) of the title compound. mp. 43–46° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-7728fca66b474411b1eb7195a7fd5293
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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