Potassium Carbonate → HCID 21452774, compound

HRID 436526Notes

Reaction equation

HRID 436526 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:16]([C:13]1[O:12][C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:18])=[O:2])=[CH:15][CH:14]=1)=[O:17]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 15841978HCID 15841978, compound

Product 1

HCID 21452774HCID 21452774, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-(5-Formyl-2-furyl)-octanoic acid methyl ester (5.04 g, 0.02 moles), methanol (30 ml) and 20% aqueous potassium carbonate (55 ml) were stirred and heated under reflux for 40 minutes. The clear solution was concentrated to 2/3 of the volume by distillation from a water bath (50° C) under reduced pressure (100 mm Hg). The residue was washed with ether (30 ml). Ether (50 ml) was added, and the resulting emulsion was acidified to pH 5 with 3N hydrochloric acid. The ethereal layer was separated. The aqueous layer was extracted with ether (30 ml). The combined ethereal extracts were washed with two 50-ml-portions of water and then dried over magnesium sulphate. The dried ethereal solution was evaporated to dryness from a water bath (60° C), at last under 15 mm Hg. The yellow crystalline residue (4.66 g), m.p. 68°-72° C, was crystallized from ethanol-water (1:3). 3.81 g (80%) of the title compound were obtained as pale yellow crystals, m.p. 70°-72° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 40 minutes
  3. concentrationThe clear solution was concentrated to 2/3 of the volume by distillation from a water bath (50° C) under reduced pressure (100 mm Hg)
  4. washThe residue was washed with ether (30 ml)
  5. additionEther (50 ml) was added
  6. customThe ethereal layer was separated
  7. extractionThe aqueous layer was extracted with ether (30 ml)
  8. washThe combined ethereal extracts were washed with two 50-ml-portions of water
  9. dry with materialdried over magnesium sulphate
  10. customThe dried ethereal solution was evaporated to dryness from a water bath (60° C)
  11. customThe yellow crystalline residue (4.66 g), m.p. 68°-72° C, was crystallized from ethanol-water (1:3)

Sources & evidence

ORD record
ord-16ea535f2ea742a38cc930255941ff07
Source dataset
uspto-grants-1977_02
Patent number
US04009187

Reaction notes

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