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

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[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]

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실험 절차

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%.