Water → 2,6-DI-Tert-butyl-4-hydroxyphenyl acetate

HRID 23808Notes

Reaction equation

HRID 23808 reaction equation
[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([O:15]C)=[CH:7][C:6]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:3])[CH3:2].[I-].[Na+].C[Si](Cl)(C)C.O>C(#N)C>[C:1]([O:4][C:5]1[C:10]([C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:9][C:8]([OH:15])=[CH:7][C:6]=1[C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 118219544-Acetoxy-3,5-di-tert-butylanisole

Product 1

HCID 111399982,6-DI-Tert-butyl-4-hydroxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The 4-acetoxy-3,5-di-tert-butylanisole obtained in Example 13 and 1.37 kg (9.14 mol) of sodium iodide were dissolved in 5.0 L of acetonitrile; thereafter, 1.16 L (9.14 mol) of trimethylsilyl chloride was added dropwise and the mixture was refluxed for 8 hours. Thereafter, the reaction mixture was cooled to room temperature, water was added and the organic layer was separated. The organic layer was washed with an aqueous solution of sodium thiosulfate and aqueous sodium chloride in that order and dried over anhydrous sodium sulfate. The crude product obtained by concentrating the organic layer was recrystallized from an ethanol/water mixed solvent and the crystal was dried to give 1.55 kg of the title compound (92.4% in yield from the 2,6-di-tert-butyl-4-methoxyphenol of Example 13).

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customthe organic layer was separated
  3. washThe organic layer was washed with an aqueous solution of sodium thiosulfate and aqueous sodium chloride in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude product obtained
  6. concentrationby concentrating the organic layer
  7. customwas recrystallized from an ethanol/water mixed solvent
  8. customthe crystal was dried

Sources & evidence

ORD record
ord-bf41ff13363546249af3d202ad5ac1e9
Source dataset
uspto-grants-2005_02
Patent number
US06852867B2

Reaction notes

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