Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 1882308Notes

Reaction equation

HRID 1882308 reaction equation
[NH:1]([C:5]1[CH:11]=[CH:10][C:8]([OH:9])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C([O-])([O-])=O.[K+].[K+].[CH3:18][CH2:19][O:20][C:21]([CH2:23]Br)=[O:22]>CC(C)=O>[CH2:19]([O:20][C:21](=[O:22])[CH2:23][O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1)[CH3:18]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 309738Ethyl 2-(4-acetamidophenoxy)acetateYield 80.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of Paracetamol (300 grams, 1.984 mol), anhydrous K2CO3 (1.80 Kg, 7.814 mmol) in anhydrous acetone (3 liters) was added ethyl bromo acetate (452 grams, 2.7 mol) and refluxed for 16 hours. Acetone was distilled and water (5 liter) was added. Crude 59 was filtered, dried, and recrystallized from a mixture of toluene:Hexane (1:5) to give pure 59 (377 grams, 80%) as a white shining powder. The melting point was found to be 104.2-106.2° C.

Workup

  1. temperaturerefluxed for 16 hours
  2. distillationAcetone was distilled
  3. additionwater (5 liter) was added
  4. filtrationCrude 59 was filtered
  5. customdried
  6. customrecrystallized from a mixture of toluene:Hexane (1:5)

Sources & evidence

ORD record
ord-f86edb5b9e5244c18dc13ef3a6a527fd
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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