Methyl iodide → 2-Isopropyl-1-methoxy-4-nitrobenzene

HRID 502629Notes

Reaction equation

HRID 502629 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13])([CH3:3])[CH3:2].[C:14]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:13][CH3:14])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5289542-Isopropyl-4-nitrophenol

Product 1

HCID 148281912-Isopropyl-1-methoxy-4-nitrobenzeneYield 89.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Isopropyl-4-nitrophenol (4.7 g, 26 mmol) was dissolved in 100 mL of acetone, and 5.4 g (39 mmol) of K2CO3 was added, followed by 14.8 g (6.5 mL, 104 mmol) of iodomethane. The reaction flask was capped and the mixture was stirred at room temperature for 17 hours. The mixture was concentrated under reduced pressure, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford 4.53 g of 3-isopropyl-4-methoxynitrobenzene.

Workup

  1. customThe reaction flask was capped
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e75d2962625a4a82901ad8dded561c73
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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