Dimethyl oxalate → HCID 178501818, compound

HRID 1004230Notes

Reaction equation

HRID 1004230 reaction equation
CC[O-].[Na+].[CH3:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)=[O:7].[CH3:16][O:17][C:18](=[O:23])[C:19](OC)=[O:20]>C1C=CC=CC=1>[OH:20][C:19](=[CH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)=[O:7])[C:18]([O:17][CH3:16])=[O:23]

Participants

5

Reactant 3

HCID 11120Dimethyl oxalateHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 2723922Sodium ethoxide

Product 1

HCID 178501818HCID 178501818, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a well stirred suspension of freshly prepared sodium ethylate (820 mg, 12 mmol) in dry benzene (10 mL), 3,4-dichloroacetophenone (1.89 g, 10 mmol) and dimethyloxalate (1.18 g, 10 mmol) dissolved in dry benzene (20 mL), were added dropwise on cooling at +5° C., and under dry nitrogen atmosphere. The resulting dark red suspension was stirred at room temperature over 4 hours. The reaction mixture was then poured into ice/2N HCl (1:1 w/w), stirred for 5 minutes and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated in vacuo to afford a pale yellow solid, which was recrystallized from acetonitrile to yield the pure ester (2.4 g, 86%),colorless needles, mp. 122-123° C.

Workup

  1. additionwere added dropwise
  2. temperatureon cooling at +5° C.
  3. stirringThe resulting dark red suspension was stirred at room temperature over 4 hours
  4. stirringstirred for 5 minutes
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto afford a pale yellow solid, which
  10. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-050d6baca13e48409d713d493dd9c6df
Source dataset
uspto-grants-2000_04
Patent number
US06048896

Reaction notes

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