Acetic Acid → 1,3-Diethyl 2-oxopropanedioate

HRID 537347Notes

Reaction equation

HRID 537347 reaction equation
Cl([O-])=O.[Na+].C(O)(=[O:7])C.[C:9]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(OCC)(=O)C>[O:7]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 23668197Sodium Chlorite

Product 1

HCID 691051,3-Diethyl 2-oxopropanedioateYield 131.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 1000 mL four-necked flask equipped with a mechanical stirrer, a dropping funnel and a thermometer, 496.8 g (1.37 mole) of 25% sodium chlorite aqueous solution, and then 26 mL (0.46 mole) acetic acid were slowly added. The pH in the reaction system was pH 4.4. Furthermore, 100 g (0.62 mole) of diethyl malonate was slowly added under room temperature, and then the mixture was stirred under room temperature for 3 hours, and then 490 mL ethyl acetate was added to the reaction system to separate the liquids. The organic layer was separated, and ethyl acetate was distilled off under reduced pressure. Toluene was added thereto to perform azeotropic dehydration and the toluene was distilled off under reduced pressure, to give 105 g of diethyl ketomalonate as an oily substance (97 yield rate).

Workup

  1. customTo a 1000 mL four-necked flask equipped with a mechanical stirrer, a dropping funnel
  2. customto separate the liquids
  3. customThe organic layer was separated
  4. distillationethyl acetate was distilled off under reduced pressure
  5. additionToluene was added
  6. distillationthe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9f266ffc4c04449da14457a0ed194621
Source dataset
uspto-grants-2014_10
Patent number
US08859803B2

Reaction notes

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