Acetic Acid → HCID 86597618, compound

HRID 910109Notes

Reaction equation

HRID 910109 reaction equation
O[CH2:2][C:3]1[C:4]2[O:12][CH:11]=[CH:10][C:5]=2[C:6](=[O:9])O[CH:8]=1.[C:13]([O-:16])(=[O:15])C.[NH4+:17].[C:18](O)(=O)C>C(OC(=O)C)C>[O:9]=[C:6]1[C:5]2[CH:10]=[CH:11][O:12][C:4]=2[C:3]([CH2:2][C:13]([O:16][CH3:18])=[O:15])=[CH:8][NH:17]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 17985442HCID 17985442, compound

Product 1

HCID 86597618HCID 86597618, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 7-(hydroxymethyl)furo[3,2-c]pyran-4-one (8.28 g, 49.8 mmol), ammonium acetate (76.8 g, 996 mmol), and glacial acetic acid and heat at reflux for 3.5 hours. Cooling to room temperature, pouring into ethylacetate, washing with water saturated aqueous sodium bicarbonate, and brine, drying over magnesium sulfate, filtering and concentrating gives 4.42 g (42%) of the title compound.

Workup

  1. temperatureat reflux for 3.5 hours
  2. washwashing with water saturated aqueous sodium bicarbonate, and brine
  3. dry with materialdrying over magnesium sulfate
  4. filtrationfiltering
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-9ff8ba7bbd6045f190cae3f09046b664
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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