Hydrochloric Acid → Ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate

HRID 1453796Notes

Reaction equation

HRID 1453796 reaction equation
[O-]CC.[Na+].[CH3:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=1)=[O:7].[C:15](OCC)(=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>C(O)C>[Cl:14][C:10]1[CH:9]=[C:8]([C:6](=[O:7])[CH2:5][C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 149331-(3-Chlorophenyl)ethanoneHCID 2723922Sodium ethoxide

Product 1

HCID 11054223Ethyl 4-(3-chlorophenyl)-2,4-dioxobutanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (117.8 g, 1.73 mol) was added in portions to a solution of 3-chloroacetophenone (178.5 g, 1.15 mol) and diethyl oxalate (188 mL, 1.39 mol) in ethanol (3 L) at 0° C. The mixture was stirred at room temperature for 1 h and was then heated at 70° C. for 2 h. After cooling, the mixture was acidified with 3M hydrochloric acid (pH˜3). The solvent was distilled off and to the mixture was added EtOAc. The organic layer was washed with water and saturated brine. The solvent was distilled off to give crude title product, which was used directly in the next step. MS (M+−1)=253.

Workup

  1. temperaturewas then heated at 70° C. for 2 h
  2. temperatureAfter cooling
  3. distillationThe solvent was distilled off and to the mixture
  4. additionwas added EtOAc
  5. washThe organic layer was washed with water and saturated brine
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-5d1a89e42caa4ae698252b594df2e294
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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