Ethyl 3-(2-methyl-3-nitrophenyl)-3-oxopropionate → 1-(2-Methyl-3-nitrophenyl)ethanone

HRID 2051232Notes

Reaction equation

HRID 2051232 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:18])[CH2:12]C(OCC)=O>O.FC(F)(F)C(O)=O.O>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11](=[O:18])[CH3:12]

Participants

4

Reactant 1

HCID 15735717Ethyl 3-(2-methyl-3-nitrophenyl)-3-oxopropionate

Product 1

HCID 126307991-(2-Methyl-3-nitrophenyl)ethanoneYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

A solution of ethyl 2-methyl-3-nitro-β-oxobenzenepropanoate (10.0 g, 39.7 mmol) in 100 mL of 30% water/trifluoroacetic acid is heated at reflux for 5 hours. The reaction mixture is cooled to room temperature, diluted with water (100 mL), and extracted with ether. The organic layer is washed with water, saturated aqueous sodium bicarbonate, and brine. Evaporation of the organic layer, followed by recrystallization of the residue gives 1-(2-methyl-3-nitrophenyl)ethanone (4.8 g, 67%), mp=49-51° C.

Workup

  1. temperatureat reflux for 5 hours
  2. extractionextracted with ether
  3. washThe organic layer is washed with water, saturated aqueous sodium bicarbonate, and brine
  4. customEvaporation of the organic layer
  5. customfollowed by recrystallization of the residue

Sources & evidence

ORD record
ord-e0dbcb9bff224d0bb0cf031cf33237d2
Source dataset
uspto-grants-1991_05
Patent number
US05017604

Reaction notes

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