Benzyl Chloride → Diethyl 2-benzylpropanedioate

HRID 1954477Notes

Reaction equation

HRID 1954477 reaction equation
C[O-].[Na+].[C:4]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[CH2:13]([O:12][C:4](=[O:11])[CH:5]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:14]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 7761Diethyl MalonateHCID 10942334Sodium Methoxide

Product 1

HCID 69090Diethyl 2-benzylpropanedioateYield 66.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 200 ml of ethanol, 16.2 g of sodium methoxide were dissolved. Into this solution, 49.5 g of diethyl malonate were dropped and gently refluxed. 37.98 g of benzyl chloride were dropped into the mixture over one hour and the mixture was refluxed for 2 hours. After the reaction was completed, the solvent was removed under reduced pressure, and water was added to the residue. After extraction with ethyl acetate, the ethyl acetate was dried with sodium sulfate anhydride. After removing the solvent under reduced pressure, followed by purification with distillation, 50 g of 2-benzylmalonic acid diethyl ester were obtained.

Workup

  1. temperaturegently refluxed
  2. temperaturethe mixture was refluxed for 2 hours
  3. customthe solvent was removed under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionAfter extraction with ethyl acetate
  6. dry with materialthe ethyl acetate was dried with sodium sulfate anhydride
  7. customAfter removing the solvent under reduced pressure
  8. distillationfollowed by purification with distillation

Sources & evidence

ORD record
ord-4cbc98226eb14b8e8513ee21037d6442
Source dataset
uspto-grants-2000_09
Patent number
US06121477

Reaction notes

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