Methyl Acrylate → Dimethyl 2,2-dichloroglutarate

HRID 407522Notes

Reaction equation

HRID 407522 reaction equation
[Cl:1][CH:2]([Cl:7])[C:3]([O:5][CH3:6])=[O:4].[CH3:8][O:9][C:10](=[O:13])[CH:11]=[CH2:12].C[O-].[Na+]>O>[Cl:1][C:2]([Cl:7])([CH2:12][CH2:11][C:10]([O:9][CH3:8])=[O:13])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8315Methyl dichloroacetateHCID 10942334Sodium Methoxide2×

Product 1

HCID 12586444Dimethyl 2,2-dichloroglutarate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 3000 liter reactor, methyl dichloroacetate and acrylic acid methyl ester are added. The stirring is controlled to start and a first controlled temperature is adjusted to 0-60° C. Then, sodium methoxide is added slowly to form a first reaction mixture. After the sodium methoxide is added, the first reaction mixture is stirred at the first controlled temperature for 1-4 hours. Subsequently, 100-300 liter of water is added to wash the first reaction mixture. The first reaction mixture is washed with water twice. The organic phase is then separated and distillation under reduced pressure is set to obtain dimethyl 2, 2-dichloroglutarate.

Workup

  1. customis adjusted to 0-60° C
  2. customto form a first reaction mixture
  3. washto wash the first reaction mixture
  4. washThe first reaction mixture is washed with water twice
  5. customThe organic phase is then separated
  6. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-e6e54001578d4e58bc96e58f1e80591b
Source dataset
uspto-grants-2014_06
Patent number
US08754256B2

Reaction notes

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