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

HRID 1728310Notes

Reaction equation

HRID 1728310 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].[CH3:14]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[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

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 145483-(3,4-Dichlorophenyl)prop-2-enoic acid

Product 1

HCID 54151376Methyl 3-(3,4-dichlorophenyl)prop-2-enoateYield 57.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3,4-Dichlorocinnamic acid (6.5g) (Ex.Aldrich), dimethylsulphate (3.77 g), potassium carbonate (4.13 g) and anhydrous acetone heated together under reflux. After cooling and filtration the acetone was removed and the residue recrystallised (80:20-hexane: ether) to give methyl 3,4-dichlorocinnamate as a colourless solid (4 g).

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. filtrationfiltration the acetone
  4. customwas removed
  5. customthe residue recrystallised (80:20-hexane: ether)

Sources & evidence

ORD record
ord-5d3b7af13a60485583fb009e1414431f
Source dataset
uspto-grants-1994_07
Patent number
US05326755

Reaction notes

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