Ethyl 2-Hydroxybutyrate → ethyl acetoacetate, sodium salt

HRID 2423503Notes

Reaction equation

HRID 2423503 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH:15]([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CC(C)=O>[O:14]=[C:15]([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 521365Ethyl 2-HydroxybutyrateHCID 131709961Jones' reagent

Product 1

HCID 85195ethyl acetoacetate, sodium saltYield 13.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones Reagent (2.67 M, 7.51 mL, 20.05 mmol) was added dropwise to ethyl 2-hydroxybutanoate (2.65 g, 20.05 mmol) in acetone (67 mL) at 0° C., then the reaction mixture was stirred for 10 minutes. Any excess Jones reagent was quenched by the addition of iso-propanol, then the reaction mixture was neutralized with saturated sodium bicarbonate, and the acetone was removed by evaporation. Water was added and the solution was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 diethyl ether:hexanes to give 346.7 mg (13%) of ethyl 2-oxobutanoate as an oil. 1H NMR (400 MHz, d6-DMSO): δ 4.19 (q, J=7 Hz, 2H), 2.80 (q, J=7 Hz, 2H), 1.24 (t, J=7 Hz, 3H), 0.94 (t, J=7 Hz, 3H).

Workup

  1. customAny excess Jones reagent was quenched by the addition of iso-propanol
  2. customthe acetone was removed by evaporation
  3. additionWater was added
  4. extractionthe solution was extracted with diethyl ether
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 1:4 diethyl ether

Sources & evidence

ORD record
ord-9d301b6d17584facb88a49a3ff977d76
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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