4-Nitrophenol → Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetate

HRID 638714Notes

Reaction equation

HRID 638714 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[I-].[Na+].[CH3:19][O:20][C:21](=[O:27])[CH2:22][O:23][CH2:24][CH2:25]Br>CC(C)=O>[CH3:19][O:20][C:21](=[O:27])[CH2:22][O:23][CH2:24][CH2:25][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 18946503Methyl (2-bromoethoxy)acetate

Product 1

HCID 59253929Methyl 2-(2-(4-nitrophenoxy)ethoxy)acetateYield 43.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-nitrophenol (5 g, 36 mmol), anhydrous K2CO3 (20 g, 145 mmol) and sodium iodide (2 grams, 13.3 mmol) in anhydrous acetone (100 ml) was added (2-bromoethoxy) acetic acid methyl ester (11 g, 56 mmol) and refluxed for 24 hours. Acetone was distilled off and water (100 ml) was added. Crude 22 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant to give pure 22 (4 g, 43.6%) as a white fluffy powder. The melting point was found to be 96-97.8° C. The structure was confirmed with IR and NMR.

Workup

  1. temperaturerefluxed for 24 hours
  2. distillationAcetone was distilled off
  3. additionwater (100 ml) was added
  4. filtrationCrude 22 was filtered
  5. customdried
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a64f066403194fab90fa2237b478c377
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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