4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 2405193Notes

Reaction equation

HRID 2405193 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-Nitro phenol (100 grams, 719 mmol), anhydrous K2CO3 (400 grams, 2.894 moles) in anhydrous acetone (950 mL) was added methyl chloroacetate (114 grams, 1.050 moles) and refluxed for 12 hours. Acetone was distilled and water (1500 mL) was added. Crude 93 was filtered, dried, and recrystallized from a mixture of Ethyl acetate:Hexane (1:5) to give pure 93 (110 grams, 72.5%) as a white fluffy powder. M.p: 97-98.4° C.

Workup

  1. temperaturerefluxed for 12 hours
  2. distillationAcetone was distilled
  3. additionwater (1500 mL) was added
  4. filtrationCrude 93 was filtered
  5. customdried
  6. customrecrystallized from a mixture of Ethyl acetate:Hexane (1:5)

Sources & evidence

ORD record
ord-1bc5ddd7c7c1451a8f8c3e432a106f2b
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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