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

HRID 1260920Notes

Reaction equation

HRID 1260920 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 the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, 1M KHSO4 solution and 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. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, 1M KHSO4 solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8d76e2becf124b579817e7a4520616b1
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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