Methane → HCID 18780058, compound

HRID 612311Notes

Reaction equation

HRID 612311 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 (5.00 g) in ethyl acetate (250 ml) was stirred with decolourising charcoal (5.0 g) for 10 mins. The mixture was filtered through Kieselguhr and the residue was washed with ethyl acetate (30 ml). The combined filtrates were hydrogenated over 5% rhodium on carbon (2.5 g) until hydrogen uptake ceased. The mixture was filtered through Kieselguhr and the residue was washed with ethyl acetate (30 ml). The combined filtrates were evaporated to give the title acid as an oil (3.64 g); νmax (Film) 3700-2800 and 1742 cm-1 ; δH [(CD3)2CO] 1.4-2.5 and 2.00 (7 H, m+s), 3.9-4.55 (4 H, m) and 7.52 (1 H, br s). (Mass spectrum: M+ (188), MH+ (189)].

Workup

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

Sources & evidence

ORD record
ord-b00a95cc044149e483cb87214e3282ee
Source dataset
uspto-grants-1999_12
Patent number
US06001997

Reaction notes

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