4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 482515Notes

Reaction equation

HRID 482515 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 700522Methyl (4-nitrophenoxy)acetateYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 56 g of 4-nitrophenol, 90 g of methyl bromoacetate, 100 g of potassium carbonate and 500 ml of dimethylformamide was stirred at room temperature for 2 days. At the end of this time, the solvent was removed by distillation under reduced pressure. The resulting residue was mixed with water and the aqueous mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was triturated with hexane to give 63.3 g of the title compound, melting at 98-99° C.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionThe resulting residue was mixed with water
  3. extractionthe aqueous mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customafter which the solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-9aafb63e5ac64ee4bfd4335bbfc2c594
Source dataset
uspto-grants-1998_08
Patent number
US05798375

Reaction notes

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