Hydrochloric Acid → Benzoylacetic acid

HRID 1524861Notes

Reaction equation

HRID 1524861 reaction equation
CC[O:3][C:4]([CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])=[O:5].[OH-].[Na+].Cl>CCO>[O:8]=[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7170Ethyl benzoylacetateHCID 14798Sodium Hydroxide

Product 1

HCID 97045Benzoylacetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl benzoyl acetate (2.88 g, 15 mmol) in EtOH (30 mL) was added 1N NaOH (30 mL). The reaction mixture was stirred at rt for 72 h. It was cooled to 0° C. and acidified with 1N HCl. EtOH was removed under reduced pressure. The aqueous layer was extracted twice with dichloromethane. The combined dichloromethane solution was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give a light yellow solid. (600 mg, 24%). MS 165.1 (M+H)+.

Workup

  1. temperatureIt was cooled to 0° C.
  2. customEtOH was removed under reduced pressure
  3. extractionThe aqueous layer was extracted twice with dichloromethane
  4. washThe combined dichloromethane solution was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a light yellow solid

Sources & evidence

ORD record
ord-7748c218b2b140e4a83c644667711e47
Source dataset
uspto-grants-2015_07
Patent number
US09079860B2

Reaction notes

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