Hydrochloric Acid → ethyl 4-(3,4-dichlorophenyl)-2,4-dioxobutanoate

HRID 539650

Reaction equation

HRID 539650 reaction equation
CC([O-])(C)C.[K+].[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1)=[O:9].[CH2:18]([O:20][C:21](=[O:27])[C:22](OCC)=[O:23])[CH3:19].Cl>C1C=CC=CC=1>[Cl:17][C:12]1[CH:11]=[C:10]([C:8](=[O:9])[CH2:7][C:22](=[O:23])[C:21]([O:20][CH2:18][CH3:19])=[O:27])[CH:15]=[CH:14][C:13]=1[Cl:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 10017017ethyl 4-(3,4-dichlorophenyl)-2,4-dioxobutanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of t-BuOK (0.05 mol, 5.6 g) in benzene (200 mL) was added dropwise a benzene (50 mL) solution of 3,4-dichloroacetophenone 5.1 (0.05 mol, 9.45 g) and diethyloxalate (0.055 mol, 8.1 g). The resultant mixture was stirred for 8 h at room temperature, then 10% aqueous HCl solution (100 mL) was added to the mixture. The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography using dichloromethane as eluent to yield the title compound. Yield: 7.5 g (52%).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-1934ae3a8e0442dda759df426fd55823
Source dataset
uspto-grants-2014_10
Patent number
US08871761B2

Linked notes

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