Dimethyl Sulfate → Methyl 3-cyano-3-(3,4-dichlorophenyl)propionate

HRID 613690Notes

Reaction equation

HRID 613690 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]([CH:9]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[CH2:10][C:11]([OH:13])=[O:12])#[N:8].COS(OC)(=O)=O>C(#N)C>[C:7]([CH:9]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[CH2:10][C:11]([O:13][CH3:1])=[O:12])#[N:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 110646173-Cyano-3-(3,4-dichlorophenyl)propionic acid

Product 1

HCID 21200323Methyl 3-cyano-3-(3,4-dichlorophenyl)propionateYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

320 g of potassium carbonate are added to a solution of 260 g of 3-cyano-3-(3,4-dichlorophenyl) propionic acid in 2.7 litres of acetonitrile. The suspension is heated under reflux in adding progressively 110 ml of dimethylsulphate. The mixture is left to return to room temperature after 15 minutes. The reaction mixture is concentrated and then taken up into 2 litres of dichloromethane. The organic phase is washed with water and then concentrated. The residue is taken up into 500 ml of methanol in order to provide the expected ester with a yield of 80%.

Workup

  1. temperatureThe suspension is heated
  2. temperatureunder reflux
  3. waitThe mixture is left
  4. concentrationThe reaction mixture is concentrated
  5. washThe organic phase is washed with water
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34a6dd7cca834ff3b540003899c8707c
Source dataset
uspto-grants-1999_12
Patent number
US06008360

Reaction notes

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