Ethyl chloroacetate → Triethyl ethane-1,1,2-tricarboxylate

HRID 339141Notes

Reaction equation

HRID 339141 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C.O>[CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])([C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 7751Ethyl chloroacetate2×HCID 7761Diethyl Malonate2×HCID 5360545Sodium

Product 1

HCID 81961Triethyl ethane-1,1,2-tricarboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

Sodium metal (23 gram, 1 mole) was dissolved in dry ethanol (500 ml) with stirring. To this 160 gram (1 mole) of diethyl malonate (compound [2]) was added in 30 minutes. The reaction mixture was cooled to 15° C. and ethyl chloroacetate (compound [1], 117 gm, 0.095 mole) was then added drop wise in 30 minutes. On completion of addition the reaction mass was refluxed for 6 hours and then poured in 2 liters of water. The organic materials were extracted with dichloromethane (three times with 500 ml). Next, the organic extracts were dried over sodium sulfate, filtered and evaporated to give an oily substance which was then vacuum distilled to give 220 gm (89% of the theoretical maximum yield) of triethyl ethane-1,1,2-tricarboxylate, compound [3].

Workup

  1. additionOn completion of addition the reaction mass
  2. temperaturewas refluxed for 6 hours
  3. extractionThe organic materials were extracted with dichloromethane (three times with 500 ml)
  4. dry with materialNext, the organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give an oily substance which
  8. distillationvacuum distilled
  9. customto give 220 gm (89% of the theoretical

Sources & evidence

ORD record
ord-86c9e29abcc54df4b18a6630f6d32b65
Source dataset
uspto-grants-2014_11
Patent number
US08889898B2

Reaction notes

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