Iodoethane → HCID 58897277, compound

HRID 1023565Notes

Reaction equation

HRID 1023565 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[CH2:12](I)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 935762-Methyl-5-nitrophenol

Product 1

HCID 58897277HCID 58897277, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-methyl-5-nitrophenol (450 mg, 2.94 mmol), ethyl iodide (356 μl, 4.41 mmol) and potassium carbonate (609 mg, 4.41 mmol) in 15 mL of acetone was heated at reflux for 2 days. The reaction mixture was filtrated, concentrated under vacuum, and the residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and concentrated under vacuum to provide the title compound (397 mg) which was directly used in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. filtrationThe reaction mixture was filtrated
  4. concentrationconcentrated under vacuum
  5. customthe residue was partitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a4c7ed408bf7489abfe0cf5ccc180a4b
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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