Potassium Hydroxide → 2-Benzyl-malonic acid monoethyl ester

HRID 2380761Notes

Reaction equation

HRID 2380761 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[K+]>CCO>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69090Diethyl 2-benzylpropanedioate

Product 1

HCID 28848672-Benzyl-malonic acid monoethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2-benzylmalonic acid diethyl ester 2.5 g (10 mmol) in EtOH (10 mL) was added 1N KOH in EtOH (8.5 mL). The solution was stirred for 1 h at room temperature. The solvent was removed under reduced pressure, and the resulting liquid dissolved in 5% NaHCO3 (30 mL), washed with EtOAc (3×10 mL), and back extracted with 5% NaHCO3 (50 mL). The combined NaHCO3 solutions were acidified to pH=3 with 1N HCl and extracted with EtOAc. The organic layer was washed with H2O, dried with Na2SO4. The solvent was removed under reduced pressure to give final product as oil, 1.4 g (74%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting liquid dissolved in 5% NaHCO3 (30 mL)
  3. washwashed with EtOAc (3×10 mL)
  4. extractionback extracted with 5% NaHCO3 (50 mL)
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with H2O
  7. dry with materialdried with Na2SO4
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-069261f2c9e54c339c0e5081d5a71c43
Source dataset
uspto-grants-2012_09
Patent number
US08257931B2

Reaction notes

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