Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 2405175Notes

Reaction equation

HRID 2405175 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-219153ef796449b992d2e5ce0b269361
Source dataset
uspto-grants-2014_08
Patent number
US08802892B2

Reaction notes

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