Potassium Carbonate → 3-(4-Nitrophenyl)pentane-2,4-dione

HRID 450089

Reaction equation

HRID 450089 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].I[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 124951-Iodo-4-nitrobenzeneHCID 31261Acetylacetone

Product 1

HCID 35304123-(4-Nitrophenyl)pentane-2,4-dioneYield 60.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of pentane-2,4-dione (4.41 g, 40 mmol), 1-iodo-4-nitrobenzene (5 g, 20 mmol) and potassium carbonate (11 g, 80 mmol) were heated in DMSO (15 ml) at 120° C. for 3 hr. The reaction mixture was cooled to room temperature, diluted with water (100 ml), and then extracted with ethyl acetate. The organic layer was washed with water, brine and dried. Evaporation gave a residue which was chromatographed over silica gel eluting with ethyl acetate/pet ether (5:95) to give 3-(4-nitrophenyl)-pentane-2,4-dione (2.67 g, 60%) as solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. customdried
  4. customEvaporation
  5. customgave a residue which
  6. customwas chromatographed over silica gel eluting with ethyl acetate/pet ether (5:95)

Sources & evidence

ORD record
ord-358a4571793c4c279af155eb1a9e2225
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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