Butyl 3-furyl(hydroxy)acetate → Butyl 2-(fur-3-yl)-2-oxo-acetate

HRID 845253Notes

Reaction equation

HRID 845253 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([OH:14])[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])=[CH:2]1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][C:3]([C:6](=[O:14])[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])=[CH:2]1

Participants

4

Reactant 2

HCID 12335665Butyl 3-furyl(hydroxy)acetateHCID 178418268HCID 178418268, compound

Product 1

HCID 13986137Butyl 2-(fur-3-yl)-2-oxo-acetateYield 83.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 39.6 g of butyl fur-3-yl-glycolate and 8.6 g of lead tetraacetate in 400 ml of absolute benzene is refluxed for 8 hours. After cooling to room temperature, the salts are filtered off and washed with benzene, and the combined benzene phases are shaken with a 10% strength sodium bicarbonate solution and a saturated sodium chloride solution. After drying over sodium sulphate, filtering off and concentrating, the oily residue is distilled in vacuo. 32.7 g (83%) of an oil, boiling point 80° C. (0.3 Torr), nD20 =1.477, are obtained.

Workup

  1. temperatureis refluxed for 8 hours
  2. filtrationthe salts are filtered off
  3. washwashed with benzene
  4. dry with materialAfter drying over sodium sulphate
  5. filtrationfiltering off
  6. concentrationconcentrating
  7. distillationthe oily residue is distilled in vacuo

Sources & evidence

ORD record
ord-56a45a5dfd974825b9f1604ecb08b06a
Source dataset
uspto-grants-1988_07
Patent number
US04757085

Reaction notes

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