Methyl iodide → HCID 22997663, compound

HRID 1166221Notes

Reaction equation

HRID 1166221 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH2:11][CH:12]=[CH2:13])[C:5]=1[OH:14])([O-:3])=[O:2].CI.[C:17](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([CH2:11][CH:12]=[CH2:13])[C:5]=1[O:14][CH3:17])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22997608HCID 22997608, compound

Product 1

HCID 22997663HCID 22997663, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-nitro-4-chloro-6-allylphenol (21.7 g), methyl iodide (28.28 g), and potassium carbonate (16.6 g) in acetone (300 ml) was refluxed for 16 hours. After cooling to room temperature and filtration, the filtrate was concentrated in vacuo to give a residue. The residue was extracted with dichloromethane. The organic layer was washed with water, dried over MgSO4, and concentrated to give crude 2-nitro-4-chloro-6-allylanisole (21.6 g, 96%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ7.69 (d, J=2.6 Hz, 1 H), 7.41 (d, J=2.6 Hz, 1 H), 5.97-5.89 (m, 1 H), 5.20-5.10 (m, 2 H), 3.88 (s, 3 H), 3.48 (d, J=6.65 Hz, 2 H).

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationfiltration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a residue
  5. extractionThe residue was extracted with dichloromethane
  6. washThe organic layer was washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-63be597710104c20a1d3b809c63983b5
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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