Hydrochloric Acid → 2,4-Dioxo-4-phenyl-butyric acid ethyl ester

HRID 1178129Notes

Reaction equation

HRID 1178129 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[C:11]1([C:17](=[O:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Na+].Cl>CN(C=O)C.O>[CH2:9]([O:8][C:1](=[O:7])[C:2](=[O:4])[CH2:18][C:17](=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 7410AcetophenoneHCID 24758Sodium hydride

Product 1

HCID 2265032,4-Dioxo-4-phenyl-butyric acid ethyl esterYield 42.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl oxalate (7.23 g, 49.47 mmol) was added to a stirred solution of 1-phenyl-ethanone (5.0 g, 41.6 mmol) in DMF (40 mL) at room temperature. The reaction mixture was cooled to 0° C. and sodium hydride (60% dispersion in oil, 2.0 g, 83.3 mmol) was added. The resulting mixture was maintained at 0° C. for 30 minutes, stirred for a further hour at room temperature and then slowly heated to 50° C. and stirred for a further 30 minutes. Chilled water was then added, the mixture was acidified with 2.4 N HCl and the resulting precipitate was filtered to afford 2,4-dioxo-4-phenyl-butyric acid ethyl ester in 42.6% yield. LC-MS purity: 85.2%.

Workup

  1. temperatureThe resulting mixture was maintained at 0° C. for 30 minutes
  2. temperatureslowly heated to 50° C.
  3. stirringstirred for a further 30 minutes
  4. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-b1d61d7d812f4f6ab782dd3f0b31a612
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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