Potassium Hydroxide → 1,1-Dimethylethyl 4-ethenylphenyl carbonate

Participants

Reaction Conditions

Reaction Steps

A solution comprising 0.49 g potassium hydroxide, 40 g of 4-acetoxystyrene, and 100 g of absolute ethanol was refluxed for 4 hours. The reaction solution was cooled to 28° C. and 13 g potassium hydroxide pellets were added over a period of 10 minutes. After an additional 30 minutes of reaction, 64 g di-tertiary-butyl-dicarbonate was charged portionwise over 20 minutes and the reaction was stirred for an additional hour at 28° C.. After aqueous washing, the reaction product was extracted with ethyl acetate. The ethyl acetate was stripped from the extraction mixture on a rotary evaporator and the residual oil was charged with 0.07 g phenothiazine. Distillation at 0.1 mm Hg gave 34.2 (64%) 4-tertiary-butoxycarbonyloxystyrene (IV).

Provenance & Evidence