Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 2169699Notes

Reaction equation

HRID 2169699 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-93bff93857154ec1b700af18c8ac9fdb
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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