Iodoethane → HCID 58897277, compound

HRID 1505367Notes

Reaction equation

HRID 1505367 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-b290b2711b4e4624a9946345ac48d2a0
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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