2-Oxobutanoic Acid → ethyl acetoacetate, sodium salt

HRID 1615682Notes

Reaction equation

HRID 1615682 reaction equation
[O:1]=[C:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[CH3:13][CH2:14]O>>[O:1]=[C:2]([CH2:6][CH3:7])[C:3]([O:5][CH2:13][CH3:14])=[O:4]

Participants

4

Procedure

To a solution of 2-oxobutanoic acid (6.0 g, 58.8 mmol) in EtOH (100 mL) was added sulfuric acid (1 mL) at room temperature. The resulting mixture was stirred for 4 h under reflux. The solvent was removed, and the residue was diluted with water (50 mL) and the pH was adjusted to ˜7 with a solution of NaOH (1 N). The mixture was extracted with EtOAc (100 mL×3). The combined organic layer was dried over sodium sulfate and concentrated to give ethyl 2-oxobutanoate (7.5 g, 98% yield). ESI MS: m/z 131 [M+H]+.

Workup

  1. temperatureunder reflux
  2. customThe solvent was removed
  3. additionthe residue was diluted with water (50 mL)
  4. extractionThe mixture was extracted with EtOAc (100 mL×3)
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4fc4ec07009b45feaad03a2526c8091d
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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