4-Nitrophenol → 2-(4-Nitrophenoxy)ethanol

HRID 322629

Reaction equation

HRID 322629 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.Cl[CH2:12][CH2:13][O:14][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[N+:7]([C:6]1[CH:5]=[CH:4][C:3]([O:10][CH2:12][CH2:13][OH:14])=[CH:2][CH:1]=1)([O-:9])=[O:8]

Participants

8

Reactant 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2628232-Chloroethoxytrimethylsilane

Product 1

HCID 853812-(4-Nitrophenoxy)ethanolYield 68.2%

Reagents, catalysts & solvents 3

HCID 10796Cesium carbonateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of p-nitrophenol (1.39 g, 10 mmol), 2-chloroethoxytrimethylsilane (3.2 ml, 20 mmol), potassium carbonate (4.15 g, 30 mmol), cesium carbonate (163 mg, 0.5 mmol), and sodium iodide (149 mg, 1 mmol) in N,N-dimethylformamide (10 ml) is heated at 75° for 19.5 hours. After cooling to ambient temperature, the mixture is diluted with ethyl acetate and filtered. The filtrate is washed with saturated aqueous sodium bicarbonate, then washed 2× with water, dried over magnesium sulfate, filtered, concentrated in vacuo, and purified on Silica gel (1:1 ethyl acetate/hexanes) to give 4-nitro-(2-Hydroxyethoxy)benzene (1.25 g).

Workup

  1. temperatureis heated at 75° for 19.5 hours
  2. filtrationfiltered
  3. washThe filtrate is washed with saturated aqueous sodium bicarbonate
  4. washwashed 2× with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified on Silica gel (1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-225d120e1f1f4c888d5ef7c380189713
Source dataset
uspto-grants-2001_04
Patent number
US06211365B1

Linked notes

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