Phenol → 4'-Nitro-3'-phenoxyacetophenone

HRID 1607667Notes

Reaction equation

HRID 1607667 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1>[N+:8]([C:7]1[CH:6]=[CH:5][C:4]([C:11](=[O:13])[CH3:12])=[CH:3][C:2]=1[O:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 104427551-(3-Chloro-4-nitrophenyl)ethanone

Product 1

HCID 117772094'-Nitro-3'-phenoxyacetophenoneYield 44%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 3'-chloro-4'-nitroacetophenone (3.0 g), phenol (2.5 g), and potassium carbonate (4.0 g) in xylene (70 ml) was refluxed for 8 hours. The insoluble was filtered off and the filtrate was concentrated under reduced pressure. The oily residue (2.7 g) was subjected to column chromatography on silica gel (70 g) eluting with toluene. The fractions containing the desired compound were combined and concentrated under reduced pressure to give crystals of 4'-nitro-3'-phenoxyacetophenone (1.7 g).

Workup

  1. temperaturewas refluxed for 8 hours
  2. filtrationThe insoluble was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washeluting with toluene
  5. additionThe fractions containing the desired compound
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b4f93731608496086e7f8a9579e2f6d
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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