Tetramethylammonium hydroxide → 1,1-Dimethylethyl 4-ethenylphenyl carbonate

Participants

Reaction Steps

To a single neck 250 ml round bottom were added 10.0 g (0.617 moles) of 4-acetoxystyrene, 13.46 g (0.617 moles) of di-t-butyldicarbonate and 52 ml (15% mole excess) of a 25 weight % solution of tetramethylammonium hydroxide and the resulting reaction mixture was stirred under nitrogen at room temperature for about 18 hours. The reaction mixture was extracted twice with ether (50 ml) and washed once with a 25 weight % solution of tetramethylammonium hydroxide (50 ml) and then twice with water (50 ml). The organic products were dried over magnesium sulfate and evaporated to dryness leaving a clear colorless oil (12.16 g, 90% yield).

Provenance & Evidence