Water → Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

HRID 2047437Notes

Reaction equation

HRID 2047437 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH:5]=[CH:6][C:7]([OH:9])=[O:8].[C:14](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH:5]=[CH:6][C:7]([O:9][CH3:14])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 145483-(3,4-Dichlorophenyl)prop-2-enoic acid

Product 1

HCID 54151376Methyl 3-(3,4-dichlorophenyl)prop-2-enoateYield 138.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dichlorocinnamic acid (21.7 g) and cesium carbonate (22.8 g) in DMF (200 mL) was added methyl iodide (7.47 mL) at 0° C., and the mixture was stirred at room temperature for 12 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, 1N aqueous potassium hydrogen sulfate solution and saturated brine and dried, and the solvent was evaporated under reduced pressure to give methyl 3,4-dichlorocinnamate (22.4 g, 97%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, 1N aqueous potassium hydrogen sulfate solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d93de3f2ead14d00829cc9ba38ae6cd4
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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