4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 2169716Notes

Reaction equation

HRID 2169716 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>[CH3:22][O:21][C:19](=[O:20])[CH2:18][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

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-Nitro phenol (100 g, 719 mmol) and anhydrous K2CO3 (400 g, 2.894 moles) 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) added. Crude 31 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:5) to give pure 31 (110 g, 72.5%) as a white fluffy powder. M.p: 97-98.4° C.

Workup

  1. temperaturerefluxed for 12 hours
  2. distillationAcetone was distilled off
  3. additionwater (1500 ml) added
  4. filtrationCrude 31 was filtered
  5. customdried
  6. customrecrystallised from a mixture of ethyl acetate:hexane (1:5)

Sources & evidence

ORD record
ord-e3551284701649ca9818fe080e4f1a84
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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