2-Oxobutanoic Acid → ethyl acetoacetate, sodium salt
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
- temperatureunder reflux
- customThe solvent was removed
- additionthe residue was diluted with water (50 mL)
- extractionThe mixture was extracted with EtOAc (100 mL×3)
- dry with materialThe combined organic layer was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4fc4ec07009b45feaad03a2526c8091d
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765760B2
Reaction notes
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