n-Methyl-p-aminophenol → HCID 22401438, compound

HRID 260345Notes

Reaction equation

HRID 260345 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11].[C:17]([O-])(=[O:19])[CH3:18].[Na+].C(=O)(O)[O-].[Na+]>O.C(O)(=O)C>[C:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([C:17](=[O:19])[CH3:18])[CH3:1])=[CH:4][CH:5]=1)(=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 5931n-Methyl-p-aminophenolHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 517045Sodium Acetate

Product 1

HCID 22401438HCID 22401438, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a flask was added 20.0 g. of 4-(N-methylamino)phenol, 20 ml. of acetic anhydride, 60 ml. of acetic acid and 10 g. of sodium acetate. The solution was warmed on a steam bath for one hour and water added to clarify the solution. The mixture was allowed to cool, more water added and the resulting solution poured onto solid sodium bicarbonate in an open vessel. The aqueous material was extracted five times with 200 ml. portions of ethyl ether, the ether extracts combined, washed with brine, then dried and concentrated to obtain the crude 4-(N-acetyl-N-methylamino)phenyl acetate which was recrystallized from a mixture of ethyl acetate, hexane and ethanol.

Workup

  1. additionTo a flask was added 20.0 g
  2. temperatureThe solution was warmed on a steam bath for one hour
  3. temperatureto cool
  4. extractionThe aqueous material was extracted five times with 200 ml
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-82e3dd0e1a454b0ea44342105fcbb72d
Source dataset
uspto-grants-1996_06
Patent number
US05527816

Reaction notes

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