Tetrahydrofuran → HCID 11139162, compound

Participants

Reaction Steps

A 10 g portion of ferulic acid, 150 mL of THF, and 80 mL of methanol were placed in a Parr pressure reactor with 1.5 grams of 10% palladium on charcoal. The reaction mixture was stirred at 30° C. under 60 psi of hydrogen for 12 hours. To remove the palladium on charcoal, the solution was vacuum filtered through celite, dried over magnesium sulfate, and condensed in vacuo. The solid was dissolved in a minimum amount of warm THF and poured into ice chilled hexanes and the solid portion recrystallized from a 5:1 mixture of ethyl acetate and water and dried on the Schlenk line. The crystals of dihydroferulic acid were acetylated by reaction with 9.6 g of acetic anhydride in the presence of 7.6 mL of pyridine. The mixture was stirred at room temperature for three hours and poured over an ice/water slurry (300 mL), to form a white precipitate that was filtered and dried on a Schlenk line, giving a 78% yield.

Provenance & Evidence