2,4,6-Trimethylphenol → 4-Chloro-6-ethyl-3-methyl-2-(2,4,6-trimethyl-phenoxy)pyridine 1-oxide

HRID 2308016Notes

Reaction equation

HRID 2308016 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]([CH2:22][CH3:23])[N+:15]=1[O-:24]>C1COCC1>[Cl:21][C:18]1[CH:17]=[C:16]([CH2:22][CH3:23])[N+:15]([O-:24])=[C:14]([O:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[C:19]=1[CH3:20]

Participants

5

Reactant 3

HCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 219123052,4-Dichloro-6-ethyl-3-methyl-pyridine 1-oxide

Product 1

HCID 219123464-Chloro-6-ethyl-3-methyl-2-(2,4,6-trimethyl-phenoxy)pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4,6-trimethylphenol in dry THF was added NaH and stirred at room temperature for 20 minutes. A solution of 2,4-dichloro-6-ethyl-3-methyl-pyridine 1-oxide was added and the resulting mixture was heated at reflux for 1.5 hour. The mixture was cooled to room temperature, quenched with water, extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give the title compound which was used directly for the next step reaction.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1.5 hour
  3. temperatureThe mixture was cooled to room temperature
  4. customquenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f89e47b65a264aaf9f6940b95d0785f3
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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