Acetaminophen → Ethyl 2-(4-acetamidophenoxy)acetate

HRID 1098697Notes

Reaction equation

HRID 1098697 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:8]([C:12]1[CH:18]=[CH:17][C:15]([OH:16])=[CH:14][CH:13]=1)[C:9]([CH3:11])=[O:10].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][O:16][C:15]1[CH:14]=[CH:13][C:12]([NH:8][C:9](=[O:10])[CH3:11])=[CH:18][CH:17]=1)[CH3:7]

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

Ethyl bromoacetate (452 g, 2.7 mol.) was added to a mixture of paracetamol (300 g, 1.984 mol) and anhydrous K2CO3 (1.80 kg, 7.814 mmol) in anhydrous acetone (3 L) and refluxed for 16 hours. Acetone was distilled and water (5 L) was added. Crude I was filtered, dried and recrystallised from a mixture of toluene:hexane (1:5) to give pure 1 (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 L) was added
  4. filtrationCrude I was filtered
  5. customdried
  6. customrecrystallised from a mixture of toluene:hexane (1:5)

Sources & evidence

ORD record
ord-f3e7a5e6b89542c99161c54dbedea2fe
Source dataset
uspto-grants-2012_03
Patent number
US08143325B2

Reaction notes

Loading…