Methyl iodide → 1-Methoxy-4-(2-methyl-2-nitropropyl)benzene

HRID 2172707Notes

Reaction equation

HRID 2172707 reaction equation
IC.[CH3:3][C:4]([N+:14]([O-:16])=[O:15])([CH3:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[C:17](=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O>[CH3:17][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([CH3:3])([N+:14]([O-:16])=[O:15])[CH3:13])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 128269024-(2-Methyl-2-nitropropyl)phenol

Product 1

HCID 128269081-Methoxy-4-(2-methyl-2-nitropropyl)benzeneYield 63.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Iodomethane (0.12 mL, 1.3 mmol) was added to a mixture of 4-(2-methyl -2-nitropropyl)phenol (300 mg, 1.5 mmol) and potassium carbonate (425 mg, 3.1 mmol) in tetrahydrofuran (20 mL) and N,N-dimethylformamide (1 mL). After refluxing overnight, the mixture was cooled and concentrated under vacuum. The residue was dissolved in ethyl acetate, washed with water, dried over anhydrous sodium sulfate and concentrated to provide crude 1-methoxy-4-(2-methyl-2-nitropropyl)benzene (200 mg, 62% yield) as yellow oil which was used directly in the next step.

Workup

  1. temperatureAfter refluxing overnight
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3e07d6589cf8436fa8b93656b0c68c90
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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