Water → Vanillyl decanoate

Participants

Reaction Conditions

Reaction Steps

Decanoic acid (25.0 g, 145 mmol), vanillyl alcohol (21.7 g, 141 mmol), and Novozym 435 (723 mg) were measured and placed in a flask (25 ml). The mixture in the flask free of a plug was heated with stirring in an oil bath at 50° C. for 48 hours. After 2 to 3 hours of stirring with heating, attachment of water on the wall of the upper part of the flask was observed. The flask was returned to room temperature, hexane (100 ml) was added to the reaction mixture, and the mixture was stirred for 1 hour. The immobilized enzyme and a small amount of precipitated vanillyl alcohol were removed by filtration. Hexane (100 ml) and 10% aqueous citric acid solution (200 ml) was added to the filtrate to allow partitioning. The aqueous layer was further extracted with hexane (150 ml), and the combined hexane layer was washed with 10% aqueous citric acid solution (100 ml), water (100 ml) and saturated brine (100 ml). The hexane layer was dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give the mixture (43.7 g) of vanillyl decanoate and decanoic acid. As a result of the analysis, the yield of vanillyl decanoate was 97.0% and the purity was 98.6 area % by HPLC. The mixture contained 3.94 wt % of decanoic acid relative to vanillyl decanoate.

Provenance & Evidence