Methane → HCID 18780058, compound

HRID 376610Notes

Reaction equation

HRID 376610 reaction equation
[C:1]([O:4][CH2:5][C:6]1[O:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].C>C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH:6]1[O:10][CH:9]([C:11]([OH:13])=[O:12])[CH2:8][CH2:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 297MethaneHCID 10330015acetyl Sumiki's acid

Product 1

HCID 18780058HCID 18780058, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-acetoxymethylfuran-2-carboxylic acid (5.00g) in ethyl acetate (250ml) was stirred with decolourising charcoal (5.0g) for 10mins. The mixture was filtered through Kieselguhr and the residue was washed with ethyl acetate (30ml). The combined filtrates were hydrogenated over 5% rhodium on carbon (2.5g) until hydrogen uptake ceased. The mixture was filtered through Kieselguhr and the residue was washed with ethyl acetate (30ml). The combined filtrates were evaporated to give the title acid as an oil (3.64g); vmax (Film) 3700-2800 and 1742cm-1 ; δH [(CD3)2CO]1.4-2.5 and 2.00 (7H, m+s), 3.9-4.55 (4H, m) and 7.52 (1H, br s). [Mass spectrum: M+ (188), MH+ (189)].

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. washthe residue was washed with ethyl acetate (30ml)
  3. filtrationThe mixture was filtered through Kieselguhr
  4. washthe residue was washed with ethyl acetate (30ml)
  5. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-a501039f385149e8ac3f2e1cc9370c4a
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

Loading…