Dimethylformamide → 2-Methoxy-4-nitrophenol acetate

HRID 393675Notes

Reaction equation

HRID 393675 reaction equation
[K].[N+:2]([C:5]1[CH:6]=C(O)C(OC)=[CH:9][CH:10]=1)([O-:4])=[O:3].[C:14]([O:17][C:18](=[O:20])[CH3:19])(=O)[CH3:15].CN([CH:24]=[O:25])C>>[C:18]([O:17][C:14]1[CH:9]=[CH:10][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][C:15]=1[O:25][CH3:24])(=[O:20])[CH3:19]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 694712-Methoxy-5-nitrophenolHCID 5462222Potassium

Product 1

HCID 499852-Methoxy-4-nitrophenol acetateYield 95%

Conditions

Temperature
80 °C

Procedure

A mixture of the potassium salt of 4-nitroguaiacol (10.15 g, 49 mmol), acetic anhydride (80 ml) DMAP (250 mg) and DMF (5 ml) was heated at 80° C. After stirring for 10 minutes, acetic arhydride was removed by evaporation and water was added to give a cream solid. The solid was collected by filtration, washed with water followed by ether and isohexanes to give 4-acetoxy-3-methoxynitrobenzene (9.84 g, 95%).

Workup

  1. customacetic arhydride was removed by evaporation and water
  2. additionwas added
  3. customto give a cream solid
  4. filtrationThe solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-6724d801b7644a749945e26cf3206907
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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