Water → Ethyl 3-(4-nitrophenoxy)benzoate

HRID 491078Notes

Reaction equation

HRID 491078 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:18]([O:17][C:15]([C:14]1[CH:13]=[C:12]([CH:22]=[CH:21][CH:20]=1)[O:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)=[O:16])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 11323654Ethyl 3-(4-nitrophenoxy)benzoateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-fluoro-1-nitrobenzene (16 mL, 150 mmol), ethyl 3-hydroxybenzoate 25 g, 150 mmol) and K2CO3 (41 g, 300 mmol) in DMF (125 mL) was heated at the reflux temp. overnight, cooled to room temp. and treated with water (250 mL). The resulting mixture was extracted with EtOAc (3×150 mL). The combined organic phases were sequentially washed with water (3×100 mL) and a saturated NaCl solution (2×100 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography (10% EtOAc/90% hexane) to afford 4-(3-ethoxycarbonylphenoxy)-1-nitrobenzene as an oil (38 g).

Workup

  1. temperaturewas heated at the reflux temp
  2. temperatureovernight, cooled to room temp.
  3. extractionThe resulting mixture was extracted with EtOAc (3×150 mL)
  4. washThe combined organic phases were sequentially washed with water (3×100 mL)
  5. dry with materiala saturated NaCl solution (2×100 mL), dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (10% EtOAc/90% hexane)

Sources & evidence

ORD record
ord-8e145567f6c84db99ab3c78b5882e611
Source dataset
uspto-grants-2009_05
Patent number
US07528255B2

Reaction notes

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