Methane → HCID 18780058, compound

HRID 1421830Notes

Reaction equation

HRID 1421830 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 (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 (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-2510c2e3334b417eb9bff1ece281c8c4
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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