Potassium Iodide → HCID 23334048, compound

HRID 904294Notes

Reaction equation

HRID 904294 reaction equation
[CH3:1][C:2]1[C:3](=[O:13])[O:4][C:5]2[C:10]([C:11]=1[OH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[O:22]1[CH2:27][CH2:26][N:25]([CH:28](Cl)[CH3:29])[CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>C(C(C)=O)C(C)C>[CH3:1][C:2]1[C:3](=[O:13])[O:4][C:5]2[C:10]([C:11]=1[O:12][CH2:29][CH2:28][N:25]1[CH2:26][CH2:27][O:22][CH2:23][CH2:24]1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 22226923HCID 22226923, compoundHCID 546870164-Hydroxy-3-methyl-2H-chromen-2-one

Product 1

HCID 23334048HCID 23334048, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Procedure

8.8 g. (0.05 mol) of 3-methyl-4-hydroxy-coumarin are solubilised in 200 ml. of methyl isobutyl ketone at 80° C., and then, at this temperature, there are added 8.3 g. (0.06 mol) of anhydrous potassium carbonate and 0.5 g. of potassium iodide. The mixture is left for 1 hour at 80° C. while stirring. In 1 hour, there is added a solution of 9.8 g. (0.065 mol) of 2-morpholino-2-chlorethane in 50 ml. of methyl isobutyl ketone. The substance is then refluxed for 8 hours, filtered while hot and evaporated under vacuum. The oil which is obtained is taken up under heat in 200 ml. of a 5% solution of sodium bicarbonate, whereafter it is cooled, and extracted with 3×100 ml of ether. It is dried over NaSO4 and then the ether is evaporated under vacuum. A brown oil is obtained which cannot be crystallised. Weight 10 g.; yield 67% (theoretical yield 14.9 g.).

Workup

  1. waitIn 1 hour
  2. additionthere is added a solution of 9.8 g
  3. temperatureThe substance is then refluxed for 8 hours
  4. filtrationfiltered while hot and
  5. customevaporated under vacuum
  6. customThe oil which is obtained
  7. temperatureunder heat in 200 ml
  8. extractionextracted with 3×100 ml of ether
  9. dry with materialIt is dried over NaSO4
  10. customthe ether is evaporated under vacuum
  11. customA brown oil is obtained which
  12. customcannot be crystallised

Sources & evidence

ORD record
ord-ce041516a6aa481b9c667b53bb34e733
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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