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

Participants

Reaction Conditions

Reaction Steps

2055 g of sodium hydrogen carbonate and 1004 g of sodium acetate were dissolved in a mixed solvent of 1.8 L of water and 15 L of THF. The resultant was cooled to −15° C., and 1.2 L of THF solution containing 2257 g of N-bromosuccinimide was added while maintaining the temperature at 0° C. or lower. Furthermore, 1200 g of furfuryl alcohol (Compound 1) was added while maintaining the temperature at 0° C. or lower, and agitated at the same temperature for 10 minutes. After confirming the end of the reaction by thin-layer chromatography, 299 g of DMAP and 2498 g of acetic anhydride were added while maintaining the temperature at 0° C. or lower. The reaction solution was heated to 30° C. and agitated at that temperature for 3.5 hours. After confirming the end of the reaction by thin-layer chromatography, the solution was cooled to 5° C., and added with 9.5 L of 2 N aqueous sodium hydroxide solution to prepare a solution of pH 6.5. This reaction solution was extracted with ethyl acetate and washed with a saturated sodium bicarbonate solution to obtain the organic layer. The solvent was distilled away under reduced pressure to obtain 1263 g of a crude product (±) 4 as a clear brown oily product (crude yield: 71.1%).

Provenance & Evidence