2,4,6-Trimethylphenol → 4-Chloro-2,5-dimethyl-6-(2,4,6-trimethyl-phenoxy)pyridine-1-oxide

HRID 968032Notes

Reaction equation

HRID 968032 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[H-].[Na+].Cl[C:14]1[C:19]([CH3:20])=[C:18]([Cl:21])[CH:17]=[C:16]([CH3:22])[N+:15]=1[O-:23]>C1COCC1>[Cl:21][C:18]1[C:19]([CH3:20])=[C:14]([O:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[N+:15]([O-:23])=[C:16]([CH3:22])[CH:17]=1

Participants

5

Reactant 3

HCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 219122022,4-Dichloro-3,6-dimethylpyridine 1-oxide

Product 1

HCID 219121314-Chloro-2,5-dimethyl-6-(2,4,6-trimethyl-phenoxy)pyridine-1-oxideYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4,6-trimethylphenol (415 mg, 3.05 mmol) in dry THF (20 ml) was treated with 60% sodium hydride in oil (122 mg, 3.05 mmol) at room temperature. After all H2 was evolved, 2,4-dichloro-3,6-dimethyl-pyridine 1-oxide (585.4 mg, 3.05 mmol) was added and the resulting mixture was heated at reflux for 2 hours. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to dryness to give solid. The solid was recrystallized from pet ether to give 802 mg (90%) of the title compound as white crystals, mp 106-107° C. 1H NMR (CDCl3) δ 7.04 (s, 1H), 6.78 (s, 2H), 2.41 (s, 3H), 2.36 (s, 3H), 2.22 (s, 3H), 2.06 (s, 6H) ppm.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. customThe mixture was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated to dryness
  7. customto give solid
  8. customThe solid was recrystallized from pet ether

Sources & evidence

ORD record
ord-5b001a278e6c4bdc9394ab45a0bc71f4
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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