Reaction #2467943

Reaction equation

2-benzylmalonic acid diethyl ester

KOH

→

final product

2-Benzyl-malonic acid monoethyl ester

Solvents

EtOH

EtOH

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe resulting liquid dissolved in 5% NaHCO3 (30 mL)
3. 3
   Washwashed with EtOAc (3×10 mL)
4. 4
   Extractionback extracted with 5% NaHCO3 (50 mL)
5. 5
   Extractionextracted with EtOAc
6. 6
   WashThe organic layer was washed with H2O
7. 7
   Dryingdried with Na2SO4
8. 8
   OtherThe solvent was removed under reduced pressure

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%).

Source