Trimethylsilyl iodide → 2,6-DI-Tert-butyl-4-hydroxyphenyl acetate

HRID 1376971Notes

Reaction equation

HRID 1376971 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].C[Si](I)(C)C.C(=O)([O-])O.[Na+]>ClCCl>[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

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 118219544-Acetoxy-3,5-di-tert-butylanisole

Product 1

HCID 111399982,6-DI-Tert-butyl-4-hydroxyphenyl acetateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Acetoxy-3,5-di-tert-butylanisole (0.50 g) was dissolved in dichloromethane (2 ml). After cooling with ice, trimethylsilyl iodide (0.31 ml) was added dropwise. The mixture was allowed to warm slowly to room temperature and stirred for 2 days; thereafter, a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture. The mixture was subjected to extraction with diethyl ether and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (15% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butylphenol [0.38 g (yield, 80%)] as a white solid.

Workup

  1. additionwas added dropwise
  2. extractionThe mixture was subjected to extraction with diethyl ether
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (15% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-86830ec96e0d44c3ac5cd129bd46e6c7
Source dataset
uspto-grants-1997_09
Patent number
US05663373

Reaction notes

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