Formic Acid → Furan-2,3-dicarbaldehyde

HRID 1830559

Reaction equation

HRID 1830559 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[O:7][CH:8]=[CH:9][C:10]=1[CH:11]=[O:12].C(O)=O.C([O-])(O)=O.[Na+].CCOC(C)=O>O>[O:7]1[CH:8]=[CH:9][C:10]([CH:11]=[O:12])=[C:6]1[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 220476222-(1,3-Dioxolan-2-yl)-3-furaldehyde

Product 1

HCID 13814199Furan-2,3-dicarbaldehydeYield 114.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2-(1,3-Dioxolan-2-yl)-3-furaldehyde (2.91 g, 17.31 mmol) is combined with formic acid (17 mL, 451 mmol) and water (4.25 mL) and stirred at rt for 18 h. The mixture is slowly transferred into a solution of NaHCO3 (45 g, 541 mmol) in water (600 mL), then stirred for 0.5 h. EtOAc (200 mL) is added, the layers separated and the aqueous layer extracted with EtOAc (2×200 mL). The combined organics are dried over Na2SO4 and concentrated to a yellow oil (3.28 g). The crude material is chromatographed over 90 g slurry-packed silica gel, eluting with 20% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 2.45 g of furan-2,3-dicarbaldehyde slightly contaminated with ethylene glycol diformate as a yellow oil. 1H NMR (CDCl3): δ 7.00, 7.67, 10.07, 10.49 ppm.

Workup

  1. stirringstirred for 0.5 h
  2. customthe layers separated
  3. extractionthe aqueous layer extracted with EtOAc (2×200 mL)
  4. dry with materialThe combined organics are dried over Na2SO4
  5. concentrationconcentrated to a yellow oil (3.28 g)
  6. customThe crude material is chromatographed over 90 g slurry-packed silica gel
  7. washeluting with 20% EtOAc/hexane
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5294a536fd254819adbbb9a11590d007
Source dataset
uspto-grants-2006_06
Patent number
US07067515B2

Linked notes

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