N-Methyl-N-nitrosourea → 4-Nitroanisole

HRID 1658185Notes

Reaction equation

HRID 1658185 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O-:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+].[CH3:12]N(N=O)C(N)=O>COCCOC>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 12699N-Methyl-N-nitrosoureaHCID 13214p-nitrophenol sodium salt

Product 1

HCID 74854-NitroanisoleYield 91.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.80 grams (5 millimoles) of anhydrous sodium p-nitrophenolate and 0.52 grams (5 millimoles) of N-methyl,N-nitrosourea were added to 25 milliliters of 1,2-dimethoxyethane kept dry with molecular sieves and a drying tube. This mixture was maintained at 0° C. for one hour and then elevated to room temperature for six hours while constant stirring was maintained. Solvent was evaporated and the residue treated simultaneously with ether and water. This mixture was shaken and the aqueous layer was removed. The ether layer was washed with potassium hydroxide (0.1 N, 3× 50 milliliters) to remove any unreacted phenol. The ether layer was washed with water (3×50 milliliters) and dried with magnesium sulfate. Filtration afforded a clear solution which was concentrated under diminished pressure to yield 0.70 grams of p-nitroanisole (about 90 percent, melting point 52°-53°. This was shown to be identical with an authentic sample.

Workup

  1. customkept dry with molecular sieves and a drying tube
  2. temperaturewas maintained
  3. customSolvent was evaporated
  4. additionthe residue treated simultaneously with ether and water
  5. stirringThis mixture was shaken
  6. customthe aqueous layer was removed
  7. washThe ether layer was washed with potassium hydroxide (0.1 N, 3× 50 milliliters)
  8. customto remove any unreacted phenol
  9. washThe ether layer was washed with water (3×50 milliliters)
  10. dry with materialdried with magnesium sulfate
  11. filtrationFiltration
  12. customafforded a clear solution which
  13. concentrationwas concentrated under diminished pressure

Sources & evidence

ORD record
ord-40f106f1dd884df8ae87a7f3654c63bc
Source dataset
uspto-grants-1976_06
Patent number
US03963698

Reaction notes

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