4-Ethenylphenyl acetate → HCID 23698959, compound

Participants

Reaction Steps

With ice cooling, 310 ml of a 1.0-M solution of potassium tertiary butoxide in tetrahydrofuran was stirred until a temperature of 5° C. was reached. To the solution, 50 grams (0.31 mol) of p-acetoxystyrene was added dropwise over 30 minutes. During this addition, the reaction solution was maintained at a temperature below 20° C. At the end of addition, the solution was allowed to stand under the conditions for 30 minutes, obtaining a yellowish orange colored tetrahydrofuran solution of potassium p-vinylphenolate. With stirring and ice water cooling, a solution of 67.28 grams (0.31 mol) of di-t-butyl dicarbonate in 60 ml of tetrahydrofuran was added dropwise to the reaction solution, which was maintained at a temperature below 20° C. At the end of addition, the reaction mixture was stirred for one hour at room temperature. It was combined with 30 ml of saturated saline water and shaken for subsequent decantation. The organic layer was dried over anhydrous sodium sulfate and the solvent distilled off. The oily residue was subjected to vacuum distillation, yielding 65 grams of a colorless oily product as a fraction of 90° to 92° C. /0.2 mmHg. It was p-t-butoxy-carbonyloxystyrene (GC 98.5%, yield 95.7%).

Provenance & Evidence