Acetic Acid → 2-oxo-2H-chromene-6-carbaldehyde

HRID 1854687Notes

Reaction equation

HRID 1854687 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[CH:5]2.C(O)(=[O:15])C>C(OCC)C.O>[O:8]1[C:9]2[C:4](=[CH:3][C:2]([CH:1]=[O:15])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]1=[O:12]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70926-Methylcoumarin

Product 1

HCID 27358312-oxo-2H-chromene-6-carbaldehydeYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

6-Methylcoumarin (400 mg, 2.50 mmol) was dissolved in 1.0 mL of diethyl ether, 1.0 mL of acetic acid, and 1.0 mL of water. After addition of ceric ammonium nitrate (5.5 g, 1.0 mmol) at room temperature, the reaction mixture was stirred at 100° C. for 1 h. The resulting mixture was diluted with water, and the solution was extracted with ethyl acetate. The extract was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 50/50) to obtain the title compound as a pale yellow powder (80 mg, 18%).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe extract was washed with water, saturated NaHCO3 aqueous solution, brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 50/50)

Sources & evidence

ORD record
ord-c13cd249df944d6592e2d65bce928ff1
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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