Furfuryl Alcohol → 6-Acetoxy-2H-pyran-3(6H)-one

Participants

Reaction Steps

500 g (5.10 mol) of furfuryl alcohol (Compound 1) was dissolved in 1.65 L of water and 6.6 L of THF in a nitrogen gas stream and cooled to 0° C. or lower. To this, a mixture of 855 g (10.2 mol) of sodium hydrogen carbonate, 418 g (5.10 mol) of sodium acetate and 953 g (5.35 mol) of N-bromosuccinimide was added by spending 40 minutes. Thereafter, the resultant was agitated for an hour, and 2,083 g (20.4 mol) of acetic anhydride was added at 0° C. or lower. Then, the resultant was heated to room temperature and agitated overnight. At the end of the reaction, 20.5 L of a saturated aqueous sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and subjected to vacuum concentration to obtain 776 g of a crude product (crude yield: 42.6%). The obtained crude product was subjected to column purification (n-Hex:AcOEt=3:1) to obtain 339 g of Compound (±) 4 as a yellow-brown oily product.

Provenance & Evidence