4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 1098702Notes

Reaction equation

HRID 1098702 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+].Cl[CH2:18][C:19]([O:21][CH3:22])=[O:20]>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 7295Methyl chloroacetateHCID 11430Potassium Carbonate

Product 1

HCID 700522Methyl (4-nitrophenoxy)acetateYield 72.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-nitrophenol (100 g, 719 mmol) and anhydrous K2CO3 (400 gm, 2.894 mol) in anhydrous acetone (950 ml) was added methyl chloroacetate (114 g, 1.050 moles) and refluxed for 12 hours. Acetone was distilled off and water (1500 ml) was added. Crude 7 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 7 (110 g, 72.5%) as a white fluffy powder with an m.p between 97-98.4° C.

Workup

  1. temperaturerefluxed for 12 hours
  2. distillationAcetone was distilled off
  3. additionwater (1500 ml) was added
  4. filtrationCrude 7 was filtered
  5. customdried
  6. customrecrystallised from a mixture of ethyl acetate:hexane (1:5)

Sources & evidence

ORD record
ord-2ccecd0e9efa4c0b8571b6d65d3f83b3
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

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