Potassium Iodide → HCID 13753877, compound

HRID 1249011Notes

Reaction equation

HRID 1249011 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].O1CCCCC1[O:21][CH2:22][C:23]#[C:24][CH2:25][CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O.CN(C)C=O>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:27][CH2:26][CH2:25][C:24]#[C:23][CH2:22][OH:21])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 13779396HCID 13779396, compound

Product 1

HCID 13753877HCID 13753877, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 9.77 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 10.90 g of 1-(tetrahydro-2-pyranoxy)-6-chloro-2-hexyne [R. B. Moffet, P. H. Seay and W. R. Reid, J. Med. Pharm. Chem., 14, 1075 (1971)]. 10.43 g of anhydrous potassium carbonate and 8.36 g of potassium iodide in 250 ml of anhydrous acetone was stirred at reflux for 18 hours. Anhydrous dimethyl formamide (100 ml) was added and reflux with stirring was continued for 52 hours. The solvent was removed in vacuo, the residue was stirred with hexane and filtered. The filtrate was concentrated in vacuo to an oil which was dissolved in 300 ml of methanol and 200 ml of 3N hydrochloric acid and heated on the steam bath for 45 minutes. As the solvent was being removed in vacuo, crystallization occurred. Water was added and the solid was filtered to give 11.78 g, mp 88°-90°, (81% yield) of 1- [2-hydroxy-4-[(6-hydroxy-4-hexynyl)oxy]-3-propylphenyl]ethanone, the titled compound.

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturereflux
  3. customThe solvent was removed in vacuo
  4. stirringthe residue was stirred with hexane
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to an oil which
  7. dissolutionwas dissolved in 300 ml of methanol
  8. temperature200 ml of 3N hydrochloric acid and heated on the steam bath for 45 minutes
  9. customAs the solvent was being removed in vacuo, crystallization
  10. additionWater was added
  11. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-5c00f337af3446f790ae1d25f2227bab
Source dataset
uspto-grants-1986_12
Patent number
US04628115

Reaction notes

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