Eugenol → Citrusin C

Participants

Reaction Steps

8.0 g of glucose pentaacetate were dissolved in 40 ml of absolute toluene, to which 3.28 g of eugenol and 2.0 g of molecular sieves 4A were then added. The mixture was stirred for about one hour. Next, 1 ml of a boron trifluoridediethyl ether complex was added to the mixture. Stirring was further continued for a day and night. After the end of the reaction, molecular sieves 4A was filtered off. The filtrate was washed twice with each 50 ml of a 0.5N aqueous solution of potassium hydroxide to remove unreacted eugenol. After washed further with water and dried with sodium sulfate, it was dried under reduced pressure to obtain 2.4 g of the intended product. According to 13C-NMR of the crystals obtained, a signal of C-1 position was detected at 102.9 ppm. It was, therefore, confirmed that the product had a β-bonding.

Provenance & Evidence