Diethyl 2-(2-(4-nitrophenyl)acetyl)malonate → 1-(4-Nitrophenyl)propan-2-one

HRID 450078

Reaction equation

HRID 450078 reaction equation
C(OC(=O)[CH:5]([C:11](=[O:22])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)C(OCC)=O)C>CS(C)=O.O>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:11](=[O:22])[CH3:5])=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

4

Reactant 1

HCID 12342271Diethyl 2-(2-(4-nitrophenyl)acetyl)malonate

Product 1

HCID 2193671-(4-Nitrophenyl)propan-2-oneYield 24%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

2-[2-(4-Nitro-phenyl)-acetyl]-malonic acid diethyl ester (1.4 g) was taken up in a mixture of DMSO (8 ml) and water (4 ml) and heated at 150° C. with stirring for 10 hr. The product was extracted with ethyl acetate (50 ml). The organic layer was washed with water, aqueous sodium bicarbonate solution and brine. The organic layer was then dried over sodium sulphate, filtered and evaporated. Purification by column chromatography over silica gel using ethyl acetate and hexane (6:94) as eluent yielded 1-(4-nitro-phenyl)-propan-2-one (160 mg, 24%).

Workup

  1. extractionThe product was extracted with ethyl acetate (50 ml)
  2. washThe organic layer was washed with water, aqueous sodium bicarbonate solution and brine
  3. dry with materialThe organic layer was then dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by column chromatography over silica gel

Sources & evidence

ORD record
ord-c2c54cfd496341b4a512b49e11d95194
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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