Acetic Acid → Ethyl 4-(4-chlorophenyl)-2,4-dioxobutanoate

HRID 1510417Notes

Reaction equation

HRID 1510417 reaction equation
[O-]CC.[Na+].[CH3:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7].[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C(O)(=O)C>C(O)C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:6](=[O:7])[CH2:5][C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 7467P-ChloroacetophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 602482Ethyl 4-(4-chlorophenyl)-2,4-dioxobutanoateYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium ethoxide (4.4 g, 64.6 mmol) in absolute ethanol (60 mL) was added 4-chloroacetophenone (5.0 g, 32.3 mmol) and the reaction mixture was stirred for five minutes at room temperature. Diethyl oxalate (7.0 mL, 51.7 mmol) in absolute ethanol (10 mL) was added and the reaction mixture was heated to reflux for 4 hours. After cooling to room temperature, acetic acid (7.0 mL) was added and the resulting light yellow solid was filtered, washed with ethanol and dried in vacuo to obtain ethyl 4-(4-chlorophenyl)-2,4-dioxobutanoate (8.3 g, 32.6 mmol).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling to room temperature
  4. filtrationthe resulting light yellow solid was filtered
  5. washwashed with ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-86141621b12840cba006355535ef628b
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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