Propionic Acid → 4,5-Di(vinyloxymethyl)cyclohexene oxide

Participants

Reaction Steps

4,5-di(hydroxymethyl)cyclohexene was epoxidized with m-chloroperbenzoic acid and thereby yielded 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture). A mixture (280 mL) of sodium carbonate 24.9 g (0.23 mol) and toluene was heated to 95° C., and 1.4 g of propionic acid was added to the mixture. Maintaining the temperature of the reaction mixture, the mixture was combined with 19 g of vinyl acetate added dropwise, and fifteen minutes later, further combined with 1.27 g (1.9 mmol) of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2. Next, 30 g (0.19 mol) of 4,5-di(hydroxymethyl)cyclohexene oxide (cis-trans mixture) was added dropwise for three hours, and a reaction was carried out in a nitrogen atmosphere while adding dropwise 62 g of vinyl acetate and holding the reaction temperature at 95° C. After the completion of dropwise addition, the mixture was stirred for one hour. As the result of gas chromatography analysis of the mixture, it is confirmed that there were produced 4,5-di(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) represented by following Formula (12) in a yield of 82% and 4-vinyloxymethyl-5-hydroxymethyl cyclohexene oxide (cis-trans mixture) in a yield of 4%. Purification of the reaction mixture by distillation yielded 31 g of 4,5-di-(vinyloxymethyl)cyclohexene oxide (cis-trans mixture) with a purity of 98%.

Provenance & Evidence