4-Aminophenol → HCID 833994, compound

HRID 1883669Notes

Reaction equation

HRID 1883669 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][NH:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 962WaterHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 833994HCID 833994, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture composed of 15 g of 4-benzyloxybenzyl chloride and 15 g of 4-aminophenol was refluxed in 200 ml of N,N-dimethylformamide for 30 minutes. After water was added to the reaction mixture, the product was extracted with ethylacetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled off, the resulting crude product was purified by silica gel column chromatography (using a 50:1 mixture of chloroform and acetone as the eluent) to obtain 11 g of 4[-N-(4-benzyloxybenzyl)-amino]phenol.

Workup

  1. extractionthe product was extracted with ethylacetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe resulting crude product was purified by silica gel column chromatography (
  6. additiona 50:1 mixture of chloroform and acetone as the eluent)

Sources & evidence

ORD record
ord-c52473d570954a18a313f614e621213b
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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