Potassium Iodide → HCID 19874534, compound

HRID 465462Notes

Reaction equation

HRID 465462 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](=[O:22])[CH3:21])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.CO.Cl>[CH2:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:2][C:3]2[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=2)=[CH:18][CH:17]=1)[C:20]([CH3:21])=[O:22]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 75065Methyl 5-(chloromethyl)-2-furoateHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 19874534HCID 19874534, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Methyl 5-chloromethyl-2-furoate (4.5 g) was added to a mixture of 4-hydroxyphenyl propan-2-one, ethylene ketal (5 g) and potassium carbonate (3.56 g) in acetone (150 ml) containing a catalytic amount of potassium iodide. The reaction mixture was stirred and heated under reflux for 4 hr., cooled and filtered. The filtrate was evaporated to an oil which was purified by column chromatography on silica gel. Elution with chloroform gave a crystalline solid which was stirred at ambient temperature for 4 hr. in a mixture of methanol (50 ml) and 2N hydrochloric acid (50 ml). The methanol was evaporated and the aqueous residue was extracted into dichloromethane. The organic extract was dried (MgSO4) and evaporated to give methyl 5-[4-acetonyl- phenoxymethyl]furan-2-carboxylate as an oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hr
  3. temperature, cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated to an oil which
  6. customwas purified by column chromatography on silica gel
  7. washElution with chloroform
  8. customgave a crystalline solid which
  9. stirringwas stirred at ambient temperature for 4 hr
  10. customThe methanol was evaporated
  11. extractionthe aqueous residue was extracted into dichloromethane
  12. extractionThe organic extract
  13. dry with materialwas dried (MgSO4)
  14. customevaporated

Sources & evidence

ORD record
ord-dd3ec5874c014e32b45d59ef33d67682
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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