4'-Hydroxyacetophenone → 1-[4-(4-Nitrophenoxy)phenyl]ethanone

HRID 1474638Notes

Reaction equation

HRID 1474638 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:20][C:17]2[CH:18]=[CH:19][C:14]([C:12](=[O:13])[CH3:11])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 2386041-[4-(4-Nitrophenoxy)phenyl]ethanoneYield 99.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 1-fluoro-4-nitrobenzene (5.0 g, 35.43 mmol) and 4-hydroxyacetophenone (4.82 g, 35.40 mmol) in DMF (40 mL) was added potassium carbonate (9.79 g, 70.86 mmol). The reaction mixture was heated at 90° C. overnight. After the completion of the reaction as confirmed by TLC, the reaction mixture was diluted with EtOAc (200 mL) and washed with water (3×30 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to afford the title compound (9.09 g, 99%) as a solid which was used as such in the next step.

Workup

  1. customAfter the completion of the reaction
  2. washwashed with water (3×30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9782b61f886a4f8f81be5b134e8ccd40
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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