Diethyl Oxalate → HCID 22034112, compound

HRID 2121608Notes

Reaction equation

HRID 2121608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9](=[O:11])[CH3:10].[C:12](OCC)(=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9](=[O:11])[CH2:10][C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 748771-(2,6-Dichlorophenyl)ethan-1-one

Product 1

HCID 22034112HCID 22034112, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2′,6′-dichloroacetophenone (12.5 g, 66 mmol) and diethyl oxalate (14.6 g, 100 mmol) in 450 mL of anhydrous toluene, cautiously add sodium hydride (60% dispersion in mineral oil, 2.8 g, 70 mmol). Cautiously heat the reaction mixture to reflux under N2 for 1 h, cool to ambient temperature and pour onto ice-cold 1M HCl. Separate the layers and extract the aqueous phase with EtOAc (2×200 mL). Wash the combined organic extracts with brine, dry over MgSO4 and evaporate to obtain the title compound which is used in the next step without further purification.

Workup

  1. temperatureCautiously heat the reaction mixture
  2. temperatureto reflux under N2 for 1 h
  3. additionpour onto ice-cold 1M HCl
  4. customSeparate the layers
  5. extractionextract the aqueous phase with EtOAc (2×200 mL)
  6. washWash the combined organic extracts with brine
  7. dry with materialdry over MgSO4
  8. customevaporate

Sources & evidence

ORD record
ord-50f93271a758439b913adde2c1cefc80
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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