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

Participants

Reaction Steps

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).

Provenance & Evidence