Iodoethane → 2-Ethoxy-1-methoxy-4-nitro-benzene

HRID 448335Notes

Reaction equation

HRID 448335 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].I[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 117901432-Ethoxy-1-methoxy-4-nitro-benzeneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-methoxy-5-nitrophenol (5.3 g, 31.3 mmol), iodoethane (14.6 g, 93.9 mmol), and potassium carbonate (43.2 g, 310 mmol) in acetone (100 mL) was heated to reflux for 4 hours. The reaction mixture was cooled, and the solvent was evaporated in vacuo. The residue was dissolved in water (250 mL) and extracted with ethyl acetate (3×75 mL). The combined organic extracts were washed with water (3×75 mL) and dried (MgSO4), and the solvent was evaporated under vacuum, providing 5.8 g of the product, in 99% yield: 1H NMR (CDCl3) δ 1.51 (t, J=7.0 Hz, 3H), 3.97 (s, 3H), 4.18 (q, J=7.0 Hz, 2H), 6.22 (dd, J=8.4 Hz, J=2.4 Hz, 1H), 6.31 (d, J=2.4 Hz, 1H), 6.70 (d, J=8.4 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated in vacuo
  5. dissolutionThe residue was dissolved in water (250 mL)
  6. extractionextracted with ethyl acetate (3×75 mL)
  7. washThe combined organic extracts were washed with water (3×75 mL)
  8. dry with materialdried (MgSO4)
  9. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-c2d78be4b550450f8649962bae2d3ef6
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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