Hydrochloric Acid → Ethyl 4-(2,4-dichlorophenyl)-2,4-dioxobutanoate

HRID 1498906Notes

Reaction equation

HRID 1498906 reaction equation
[O-]CC.[Na+].C(O)C.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16](=[O:18])[CH3:17].[C:19](OCC)(=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>O1CCCC1.C(Cl)(Cl)Cl>[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[C:16](=[O:18])[CH2:17][C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 166932',4'-DichloroacetophenoneHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 22997478Ethyl 4-(2,4-dichlorophenyl)-2,4-dioxobutanoateYield 78.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 20% sodium ethoxide-ethanol solution (17 g) was added to tetrahydrofuran (100 ml), and the mixture was cooled to 0° C. It took 60 minutes to dropwise add a solution of 2′,4′-dichloroacetophenone (9.45 g) and diethyl oxalate (7.30 g) in tetrahydrofuran (100 ml) to the mixture. After the completion of the dropping, the mixture was allowed to warm to a room temperature and stirred for 2 hours. To the mixture, 2-N hydrochloric acid (200 ml) and chloroform (200 ml) were added. The organic layer was collected by separation and dried over anhydrous magnesium sulfate, and the solvent was distilled off. Thus, the title compound (11.3 g, 78%) as a light-brown oily substance was obtained.

Workup

  1. temperatureto warm to a room temperature
  2. customThe organic layer was collected by separation
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8d9a8dc1f44042208113ba2f3fba5115
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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