Acetone → CID 4301653

HRID 29145Notes

Reaction equation

HRID 29145 reaction equation
[O-]CC.[Na+].[Na].[C:6]([O:13][CH2:14][CH3:15])(=[O:12])[C:7]([O:9]CC)=O.[CH3:16][C:17]([CH3:19])=[O:18].S(=O)(=O)(O)O>C(O)C.O>[OH:9][C:7](=[CH:16][C:17](=[O:18])[CH3:19])[C:6]([O:13][CH2:14][CH3:15])=[O:12]

Participants

8

Reactant 5

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 5360545Sodium2×

Product 1

HCID 4301653CID 4301653Yield 101%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 2-liter three-neck round-bottom flask equipped with a dropping funnel and a paddle stirrer a solution of sodium ethoxide is prepared by reacting metallic sodium (7.74 g, 340.00 mmol, 1.2 eq) in anhydrous ethanol (800 ml) at ambient temperature until the metallic sodium has been completely consumed. A solution of diethyl oxalate (37.20 mL, 280.00 mmol, 1.0 eq) in acetone (10.30 mL, 280.00 mmol, 1.0 eq) is subsequently added dropwise at ambient temperature. The reaction medium is maintained with vigorous stirring for 2 hours. The reaction medium is subsequently concentrated under vacuum. The crude reaction product is diluted in water (200 ml). Ice (100 g) is added, followed by concentrated sulfuric acid (20 ml) in small portions, until a clear orange solution is obtained. The resulting aqueous phase is extracted with ethyl acetate (3×300 mL). The organic phases are combined, dried over MgSO4 and then concentrated under vacuum. The crude reaction product is dried under vacuum to give, quantitatively, the expected product (m=44.71 g).

Workup

  1. customis prepared
  2. customat ambient temperature
  3. customhas been completely consumed
  4. temperatureThe reaction medium is maintained
  5. concentrationThe reaction medium is subsequently concentrated under vacuum
  6. customThe crude reaction product
  7. customis obtained
  8. extractionThe resulting aqueous phase is extracted with ethyl acetate (3×300 mL)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated under vacuum
  11. customThe crude reaction product
  12. customis dried under vacuum
  13. customto give

Sources & evidence

ORD record
ord-f6134be461a14511880bb3bc6c707851
Source dataset
uspto-grants-2008_09
Patent number
US07420087B2

Reaction notes

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