1-Chloro-2,4-Dinitrobenzene → Ethyl 2-(2,4-dinitrophenyl)-3-oxobutanoate

HRID 2390927Notes

Reaction equation

HRID 2390927 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH3:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23].Cl>O1CCCC1>[N+:19]([C:16]1[CH:15]=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=[CH:18][C:17]=1[CH:5]([C:4](=[O:3])[CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydride

Product 1

HCID 230687Ethyl 2-(2,4-dinitrophenyl)-3-oxobutanoateYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (417 mmol) was added to a solution of ethyl 3-oxobutanoate (129 mmol) in tetrahydrofuran (350 mL). 1-Chloro-2,4-dinitrobenzene (123 mmol) was added and the resulting suspension was maintained for 24 h at rt. The pH was adjusted to 5 by the addition of 3 M hydrochloric acid and the resulting solution was extracted with diethyl ether (300 mL). The organic layer was washed with water (3×300 mL), dried (magnesium sulfate), and concentrated to provide ethyl 2-(2,4-dinitrophenyl)-3-oxobutanoate in 98% yield as a brown solid.

Workup

  1. extractionthe resulting solution was extracted with diethyl ether (300 mL)
  2. washThe organic layer was washed with water (3×300 mL)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80edf1cd4fe44baaa9637f1b612a755c
Source dataset
uspto-grants-2012_09
Patent number
US08273891B2

Reaction notes

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