Acetaminophen → methyl [4-(acetylamino)phenoxy]acetate

HRID 1070520Notes

Reaction equation

HRID 1070520 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21]>CC(C)=O>[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 10955184methyl [4-(acetylamino)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Acetaminophenol (1.51 g), potassium carbonate (1.38 g) and methyl bromoacetate (1.0 ml) were combined in acetone (40 ml) and heated to reflux for 5 hours. The mixture was allowed to cool to room temperature, filtered and evaporated. The residue was dissolved in ethyl acetate, washed with water and then with brine then dried, filtered and evaporated to give the subtitle compound (2.32 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialwith brine then dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-52510b13a6ff4eafa460c0815e9f1d83
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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