Ethyl benzoylacetate → Benzoylacetic acid

HRID 2245813Notes

Reaction equation

HRID 2245813 reaction equation
[OH-].[Na+].[C:3]([CH2:11][C:12]([O:14]CC)=[O:13])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O>[C:3]([CH2:11][C:12]([OH:14])=[O:13])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 14798Sodium Hydroxide

Product 1

HCID 97045Benzoylacetic acidYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (0.4 g) was dissolved in water (10 mL), and ethyl benzoylacetate (2.14 g: 90% pure, made by Aldrich) was added and this was agitated overnight at room temperature. The reaction product was washed with ether, then 10% dilute sulfuric acid (4.9 g) was added and the reaction product was extracted with ether. The ether extract was dried by adding excess anhydrous sodium sulfate, and the anhydrous sodium sulfate was removed by filtration. The ether was then removed with a rotary evaporator, yielding benzoylacetic acid (yield 1.05 g).

Workup

  1. washThe reaction product was washed with ether
  2. addition10% dilute sulfuric acid (4.9 g) was added
  3. extractionthe reaction product was extracted with ether
  4. extractionThe ether extract
  5. customwas dried
  6. additionby adding excess anhydrous sodium sulfate
  7. customthe anhydrous sodium sulfate was removed by filtration
  8. customThe ether was then removed with a rotary evaporator

Sources & evidence

ORD record
ord-696f6de21d2842b19c8899a67a72ad17
Source dataset
uspto-grants-2010_03
Patent number
US07683195B2

Reaction notes

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