Water → tert-Butyl 4-(prop-1-en-2-yl)phenyl carbonate

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Reaction Steps

A mixture of 5.64 g of p-hydroxy-α-methylstyrene, synthesized by base-catalyzed cleavage of 2,2-bis(p-hydroxyphenyl)propane, and 6.5 g of potassium tert-butoxide in 50 mL of dry tetrahydrofuran was stirred for 10 minutes, then a tetrahydrofuran solution of 12.7 g of di-tert-butyl dicarbonare was added. The resulting gelatinous mixture was mechanically stirred for 20 minutes, and then poured into cold water. After work-up, a crude product was obtained by evaporation of the extraction solvent (ethyl acetate). Purification was achieved by high pressure liquid chromatography with hexane as eluent to give 8.03 g (81%) of the pure p-tert-butoxycarbonyloxy-α-methylstyrene.

Provenance & Evidence