Water → 2-Methyl-3-nitroanisole

HRID 1505345Notes

Reaction equation

HRID 1505345 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[H-].[Na+].[CH3:14]I.O>CN(C=O)C>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 795792-Methyl-3-nitrophenol

Product 1

HCID 785542-Methyl-3-nitroanisoleYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-3-nitrophenol (15.3 g, 100 mmol) in DMF (150 mL) was added sodium hydride (60% in mineral oil, 2.6 g, 110 mmol) at 0° C. and the mixture was stirred for 30 minutes at room temperature. Methyl iodide (28.4 g, 200 mmol) was added and the mixture was heated to 80° C. for 5 hours. Water (100 mL) was added and the mixture was extracted with ethyl acetate (3 times 100 mL). The combined ethyl acetate phases were dried over sodium sulphate and concentrated under vacuum to give a residue, which was purified by column chromatography on silica gel (PE:EtOAc=5:1). Evaporation afforded the title compound as a yellow solid (14.4 g).

Workup

  1. temperaturethe mixture was heated to 80° C. for 5 hours
  2. extractionthe mixture was extracted with ethyl acetate (3 times 100 mL)
  3. dry with materialThe combined ethyl acetate phases were dried over sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by column chromatography on silica gel (PE:EtOAc=5:1)
  7. customEvaporation

Sources & evidence

ORD record
ord-8094c1cc322245e492c576fd17caa45e
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

Loading…