4-Nitrophenol → Methyl (4-nitrophenoxy)acetate

HRID 1882326Notes

Reaction equation

HRID 1882326 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-e2d3c5df375d4fe4b7498aa37273664d
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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