4-Coumaric acid → HCID 3126208, compound

HRID 1597715Notes

Reaction equation

HRID 1597715 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:11]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1)[CH2:12][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3224-Coumaric acidHCID 11430Potassium Carbonate

Product 1

HCID 3126208HCID 3126208, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 50 ml of dimethyl sulfoxide was suspended 15.5 g of 4-hydroxycinnamic acid, 30.0 g of bromoheptyl and 50.0 g of potassium carbonate, and were vigorously stirred for 10 hours with a mechanical stirrer while the flask was heated in oil bath under reflux. After the obtained reaction mixture was cooled, it was filtered through Celite, and the resultant residue was washed with 300 of ethyl acetate. After 500 ml of water was added to the washed mixture and the mixture was extracted with 2.5 liter of ethyl acetate, the obtained extract (organic layer) was concentrated by removing the solvent in vacuo. To the resultant residue was added 100 ml of ethanol, an aqueous solution (20 ml) containing sodium hydroxide of 10 g was added and stirred at 80° C. for 1 hour. After the resultant reaction mixture was cooled, the precipitated crystals were filtered in vacuo, and the residue was washed with 100 ml of ethanol. The washed residue was placed in 300 of dilute hydrochloric acid of 40° C., and stirred for 1 hour. The reaction mixture was filtered in vacuo and dried to obtain the above compound (e) of 19.1 g (yield: 78%).

Workup

  1. temperaturewas heated in oil bath
  2. temperatureunder reflux
  3. customAfter the obtained reaction mixture
  4. temperaturewas cooled
  5. filtrationit was filtered through Celite
  6. washthe resultant residue was washed with 300 of ethyl acetate
  7. additionAfter 500 ml of water was added to the washed mixture
  8. extractionthe mixture was extracted with 2.5 liter of ethyl acetate
  9. extractionthe obtained extract (organic layer)
  10. concentrationwas concentrated
  11. customby removing the solvent in vacuo
  12. additionTo the resultant residue was added 100 ml of ethanol
  13. additionan aqueous solution (20 ml) containing sodium hydroxide of 10 g
  14. additionwas added
  15. stirringstirred at 80° C. for 1 hour
  16. customAfter the resultant reaction mixture
  17. temperaturewas cooled
  18. filtrationthe precipitated crystals were filtered in vacuo
  19. washthe residue was washed with 100 ml of ethanol
  20. customwas placed in 300 of dilute hydrochloric acid of 40° C.
  21. stirringstirred for 1 hour
  22. filtrationThe reaction mixture was filtered in vacuo
  23. customdried

Sources & evidence

ORD record
ord-22acd472366247d391881335b7865a25
Source dataset
uspto-grants-1998_04
Patent number
US05736067

Reaction notes

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