3-Chlorophenol → 3'-(3-Chlorophenoxy)-4'-nitroacetophenone

HRID 1607669Notes

Reaction equation

HRID 1607669 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].[Cl:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1>[Cl:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[O:21][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]

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 104427551-(3-Chloro-4-nitrophenyl)ethanone

Product 1

HCID 100856823'-(3-Chlorophenoxy)-4'-nitroacetophenoneYield 54.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 3'-chloro-4'-nitroacetophenone (3 g), m-chlorophenol (2.3 g) and potassium carbonate (2.5 g) in xylene (30 ml) was stirred and refluxed for 7 hours. The insoluble was filtered and the filtrate was washed with an aqueous solution of sodium hydroxide (10%) and water, dried, and concentrated. The residue was purified by column chromatography on silica gel eluting with toluene to give an oil of 3'-(3-chlorophenoxy)-4'-nitroacetophenone (2.4 g).

Workup

  1. temperaturerefluxed for 7 hours
  2. filtrationThe insoluble was filtered
  3. washthe filtrate was washed with an aqueous solution of sodium hydroxide (10%) and water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel eluting with toluene

Sources & evidence

ORD record
ord-fac9fdbc62ca4b35887e2b19a1194ae9
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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