4-Chlorophenyl Acetate → Triacetylresveratrol

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A 10 ml Schlenk tube equipped with magnetic stirrer was charged with 119 mg (0.7 mmol) of 4-acetoxychlorobenzene, 200 mg (0.84 mmol, 1.2 eq) of 3,5-diacetoxystyrene, 177 mg (0.84 mmol, 1.2 eq) of potassium triphosphate, 5 mg of diadamantyl-n-butylphosphine (0.014 mmol, 2 mol %) and 3.7 mg (0.003 mmol, 0.5 mol %) of tris(dibenzylideneacetone)-dipalladium chloroform complex. The tube was evacuated and flushed with argon three times, and 2 ml of de-aerated DMAc was added under inert conditions. The reaction was carried out under stirring for 15.5 hours at 120° C. Work-up of the reaction mixture following the procedure of Example 5 gave (E)-3,4′,5-triacetoxystilbene.

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