Carbon Dioxide → Furan-2,3-dicarboxylic Acid

Temperature

-78 °C

n-Butyllithium (2.5M in hexanes, 196 mL, 491 mmol) was introduced into a dry 3 L 3-necked flask fitted with an addition funnel, argon inlet, and mechanical stirrer. The mixture was diluted with dry THF (500 mL), and cooled to −78° C. 3-furoic acid (25 g, 223 mmol) was added as solution in THF (500 mL) dropwise. The mixture was stirred for 1.5 h, at which point dry carbon dioxide was bubbled through the reaction mixture for 1 h. After warming gradually to −10° C., the resultant thick white slurry was treated with aqueous HCl (2 N, 446 mL). The two layers were separated, and the aqueous layer was extracted with EtOAc (3×300 mL). The combined organics were dried (Na2SO4), filtered, and concentrated to afford crude furan-2,3-dicarboxylic acid as an orange solid (44 g) which was used without further purification. 1H NMR (300 MHz, d6-acetone) δ 7.06 (d, J=1.7, 1), 7.97 (d, J=1.7, 1), 10.7 (bs, 2H); TLC(CHCl3/MeOH/H2O 6:4:1) Rf=0.56.

1. customfitted with an addition funnel, argon inlet, and mechanical stirrer
2. customwas bubbled through the reaction mixture for 1 h
3. temperatureAfter warming gradually to −10° C.
4. additionthe resultant thick white slurry was treated with aqueous HCl (2 N, 446 mL)
5. customThe two layers were separated
6. extractionthe aqueous layer was extracted with EtOAc (3×300 mL)
7. dry with materialThe combined organics were dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-bd0fb4fa2de84947a10996c08f855202

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304406B2