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

HRID 501857Notes

Reaction equation

HRID 501857 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 g, 13.3 mmol) in anhydrous acetone (100 ml) was added (2-bromoethoxy)acetic acid methyl ester (11 g, 56 mmol) and then refluxed for 24 hours. Acetone was distilled off and water (100 ml) was added. Crude 42 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant to give pure 42 (4 g, 43.6%) as a white fluffy powder with an m.p. between 96-97.8° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. distillationAcetone was distilled off
  3. additionwater (100 ml) was added
  4. filtrationCrude 42 was filtered
  5. customdried
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8b3d6ab211ad4bf9a16f99c70393b2e4
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

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