Acetic Acid → Phenol, 4,4'-(dimethylsilylene)bis[2,6-bis(1,1-dimethylethyl)-

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Reaction Steps

To a solution of 9.8 g (16 mmol) of dimethylbis(3,5-di-tert-butyl-4-trimethylsilyloxyphenyl)silane in 50 ml of tetrahydrofuran is slowly added 10.6 g (32 mmol) of tetrabutylammonium fluoride trihydrate. The reaction mixture is stirred for 1 hour at room temperature and to it is added 0.8 g (14 mmol) of glacial acetic acid. The reaction mixture is poured into 250 ml of water and the solution is extracted (2×125 ml) with methylene chloride. The organic phase is dried over anhydrous sodium sulfate and the solvent is removed in vacuo to give 7.3 g of an orange residue which crystallizes on standing. The residue is recrystallized from heptane to give 1.2 g (17%) of a white solid; mp. 186°-188° C.

Provenance & Evidence