Ethyl benzoylacetate → Benzoylacetic acid

HRID 323931Notes

Reaction equation

HRID 323931 reaction equation
[C:1]([CH2:9][C:10]([O:12]CC)=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>>[C:1]([CH2:9][C:10]([OH:12])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 14798Sodium Hydroxide

Product 1

HCID 97045Benzoylacetic acidYield 66.3%

Procedure

To 11.6 g (60.3 mmol) of ethyl benzoylacetate, was added 60 mL of a 1 N aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 16 hours. After removing organic substances by ether, the reaction solution was acidified by adding concentrated hydrochloric acid while cooling the solution in an ice bath to give a precipitate. The precipitate was collected by filtration, washed with cold water, and dried under reduced pressure. As a result, 6.56 g (40.0 mmol, 66.3%) of benzoylacetic acid was obtained as a pale yellow powder.

Workup

  1. customAfter removing organic substances by ether
  2. additionby adding concentrated hydrochloric acid
  3. temperaturewhile cooling the solution in an ice bath
  4. customto give a precipitate
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with cold water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-57c060725e204ffebeb1f0d064eb687c
Source dataset
uspto-grants-2001_04
Patent number
US06215016B1

Reaction notes

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