Methyl Acetate → Dimethyl malonate

HRID 326003Notes

Reaction equation

HRID 326003 reaction equation
[C]=O.[CH3:3][O:4][C:5](=[O:8])[CH2:6]Cl.C[O-].[K+].[CH3:12][O:13][C:14](=[O:16])C.COC(=O)COC>>[CH3:3][O:4][C:5](=[O:8])[CH2:6][C:14]([O:13][CH3:12])=[O:16]

Participants

6

Reactant 5

HCID 6584Methyl AcetateHCID 7295Methyl chloroacetateHCID 80507Methyl methoxyacetateHCID 23664618Potassium methoxideHCID 178418416HCID 178418416, compound

Product 1

HCID 7943Dimethyl malonateYield 90%

Procedure

In a one-liter glass flask equipped with stirrer, 2 dropping funnels, a reflux condenser, a glass electrode and a glass inlet tube for carbon monoxide, 108.5 g (1 mole) of chloroacetic acid methyl ester is reacted for 61/2 hours with 1 mole of potassium methylate (28.75% solution in methanol) in the presence of 10 g of Co2 (CO)8, at 70° C., 0.8 at. CO, and a pH of approximately 8.5. The processing yields 119 g of malonic acid dimethyl ester (90% yield), and small amounts of acetic acid methyl ester and methoxyacetic acid methyl ester, plus 5 g of higher-boiling substances.

Workup

  1. customIn a one-liter glass flask equipped with stirrer
  2. customat 70° C.

Sources & evidence

ORD record
ord-fce572774b134ba38089f91b5b19f90f
Source dataset
uspto-grants-1984_04
Patent number
US04443624

Reaction notes

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