Dichloromethane → Ethyl 3-(3-methyl-4-nitrophenyl)-3-oxopropanoate

HRID 2243267Notes

Reaction equation

HRID 2243267 reaction equation
ClCCl.C[C:5]1([CH3:13])[O:10][C:9](=[O:11])[CH2:8][C:7](=[O:12])O1.CN(C1C=CC=CN=1)C.[CH3:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34])C(Cl)=O>C(O)C>[CH3:23][C:24]1[CH:25]=[C:26]([C:7](=[O:12])[CH2:8][C:9]([O:10][CH2:5][CH3:13])=[O:11])[CH:30]=[CH:31][C:32]=1[N+:33]([O-:35])=[O:34]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 218852-DimethylaminopyridineHCID 30157953-Methyl-4-nitrobenzoyl chloride

Product 1

HCID 50999720Ethyl 3-(3-methyl-4-nitrophenyl)-3-oxopropanoateYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a dichloromethane solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (10 g) and dimethylaminopyridine (17 g), a dichloromethane solution of 3-methyl-4-nitro-benzoyl chloride (14 g) was added dropwise under ice cooling. After stirring at room temperature for 3 hours and then adding 100 ml of ethanol, the mixture was refluxed for 2 hours. After cooling, the solvent was distilled off under the reduced pressure. The residue was dissolved in ethyl acetate and washed with 1N aqueous solution of hydrochloric acid. After drying the organic layer with sodium sulfate, the solvent was distilled off and the obtained residue was purified by silica gel column chromatography to obtain ethyl 3-(3-methyl-4-nitro-phenyl)-3-oxo-propionate (12.4 g). mp; 207-211° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off under the reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1N aqueous solution of hydrochloric acid
  6. dry with materialAfter drying the organic layer with sodium sulfate
  7. distillationthe solvent was distilled off
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a70c6be62c474989ab8dc480f86ef94a
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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