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

HRID 1882319Notes

Reaction equation

HRID 1882319 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 grams, 36 mmol), anhydrous K2CO3 (20 grams, 145 mmol) and sodium iodide (2 grams, 13.3 mmol) in anhydrous acetone (100 mL) was added (2-Bromoethoxy)acetic acid methyl ester (11 grams, 56 mmol) and refluxed for 24 hours. Acetone was distilled and water (100 mL) was added. Crude 74 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant give pure 74 (4 grams, 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. IHNMR (CDCl3+DMSO) δ 3.72 (s, 3H, ester), 3.94 (t, 2H, OCH2), 4.18 (s, 2H, OCH2), 4.30 (t, 2H, OCH2), 7.08 (d, 2H, Ar), 8.18 (d, 2H, Ar).

Workup

  1. temperaturerefluxed for 24 hours
  2. distillationAcetone was distilled
  3. additionwater (100 mL) was added
  4. filtrationCrude 74 was filtered
  5. customdried
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-85d42dd2f03e42b7be13dc416c54411a
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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