Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 1957821Notes

Reaction equation

HRID 1957821 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+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:9][C:8]1[CH:10]=[CH:11][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1)[CH3:24]

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 g, 1.984 mol), and anhydrous K2CO3 (1.80 Kg, 7.814 mmol) in anhydrous acetone (3 liters) was added ethyl bromoacetate (452 gr, 2.7 mol) and refluxed for 16 hours. Acetone was distilled off and water (5 liter) was added. Crude 13 was filtered, dried and recrystallised from a mixture of toluene:hexane (1:5) to give pure 13 (377 g, 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 off
  3. additionwater (5 liter) was added
  4. filtrationCrude 13 was filtered
  5. customdried
  6. customrecrystallised from a mixture of toluene:hexane (1:5)

Sources & evidence

ORD record
ord-1ddc43538ea3433184e3af311a8b5589
Source dataset
uspto-grants-2013_04
Patent number
US08409559B2

Reaction notes

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