Acetaminophen → p-(2,4-Dimethoxybenzyloxy)acetanilide

HRID 1448441Notes

Reaction equation

HRID 1448441 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:21]=1[CH2:22]Cl>CN(C)C=O>[CH3:18][O:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:21]=1[CH2:22][O:11][C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 185052611-(Chloromethyl)-2,4-dimethoxybenzene

Product 1

HCID 20379816p-(2,4-Dimethoxybenzyloxy)acetanilide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

p-Acetylaminophenol (15.1 g, 0.1 M) in dimethyl formamide (30 ml) containing potassium carbonate (1.36 g, 0.1 M) is treated with 2,4-dimethoxybenzyl chloride (1.86 g, 0.1 M). The mixture is then heated at 130° C. for 3 hours, then the solvent removed by evaporation under reduced pressure. The residue is treated with water, and the precipitate filtered off and recrystallized from ethanol to afford p-(2,4-dimethoxybenzyloxy)acetanilide.

Workup

  1. customthe solvent removed by evaporation under reduced pressure
  2. additionThe residue is treated with water
  3. filtrationthe precipitate filtered off
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b3542056d8ca4db1872a42fd1f6c7bb5
Source dataset
uspto-grants-1979_12
Patent number
US04180509

Reaction notes

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