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

HRID 1957862Notes

Reaction equation

HRID 1957862 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 59 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant to give pure 59 (4 g, 43.6%) as a white fluffy powder. M.p: 96-97.8° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. distillationAcetone was distilled off
  3. additionwater (100 ml) was added
  4. filtrationCrude 59 was filtered
  5. customdried
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e1fdf190586b47d2bdae6094ee54b428
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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