Ethyl chloroacetate → Diethyl Malonate

HRID 326004Notes

Reaction equation

HRID 326004 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5]Cl)[CH3:2].[C]=O.[OH-:10].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 14798Sodium HydroxideHCID 178418416HCID 178418416, compound

Product 1

HCID 7761Diethyl MalonateYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a pressure vessel with a capacity of 7.5 liters, there are combined 20 g of Co2 (CO)8 in 2.5 liters of ethanol, and 612.5 g (5 moles) of chloroacetic acid ethyl ester, in a nitrogen atmosphere. Then the apparatus is scavenged three times with carbon monoxide, and a CO pressure of 7 bars is established. After the reaction temperature of 55° C. is reached, an 11.8% ethanolic solution of NaOH is pumped in by a proportioning pump at a CO pressure of 8 bars, in such a manner that a pH value of about 7.0 is sustained during the reaction. The reaction solution is constantly agitated during the reaction by means of a circulation pump. After 5 hours of reaction time a transformation of 79.2% is achieved. The reaction solution is separated from the NaCl on a rotary evaporator and distilled. 596 grams of malonic acid diethyl ester (94% yield) are obtained, and 20 g of acetic acid ethyl ester (5.7% yield) plus 127 g of chloroacetic acid ethyl ester.

Workup

  1. customIn a pressure vessel with a capacity of 7.5 liters, there are combined
  2. customAfter the reaction temperature of 55° C.
  3. customin such a manner that a pH value of about 7.0 is sustained during the reaction
  4. customAfter 5 hours of reaction time a transformation of 79.2%
  5. customThe reaction solution is separated from the NaCl on a rotary evaporator
  6. distillationdistilled

Sources & evidence

ORD record
ord-048af546fcba47d18fd054d7d42170ae
Source dataset
uspto-grants-1984_04
Patent number
US04443624

Reaction notes

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