4-Aminophenol → HCID 59253931, compound

HRID 638717Notes

Reaction equation

HRID 638717 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:14]([O:21][CH2:22][C:23](Cl)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(C)=O>[CH2:14]([O:21][CH2:22][C:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 177085Benzyloxyacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 59253931HCID 59253931, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To mixture of 4-aminophenol (20 g, 183.2 mmol) and sodium bicarbonate (17 grams, 202 mmol) in acetone (150 ml) at 0° C. was added benzyloxy acetyl chloride (40 g, 216.8 mmol) drop wise, followed by stirring at room temperature for 20 hours. The solids were filtered off, and cold water (500 ml) was added. Crude 26 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), water (2×100 ml), dried over sodium sulphate and distilled. The crude 26 was purified by column chromatography on silica gel using chloroform as eluant to get pure 26 (23 g, 48.9%) as a light orange syrup.

Workup

  1. filtrationThe solids were filtered off
  2. additioncold water (500 ml) was added
  3. extractionCrude 26 was extracted into chloroform
  4. washwashed with 5% sodium bicarbonate solution (2×100 ml), water (2×100 ml)
  5. dry with materialdried over sodium sulphate
  6. distillationdistilled
  7. customThe crude 26 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-784271a49b2f4edb845d3d3c461068ce
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Reaction notes

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