Potassium Carbonate → 3-(Heptyloxy)benzoic acid

HRID 440212Notes

Reaction equation

HRID 440212 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:9](=[O:12])([O-])[O-:10].[K+].[K+].CN(C)[C:17](=[O:19])[CH3:18]>O>[CH2:2]([O:19][C:17]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:18]=1)[C:9]([OH:10])=[O:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 31374Dimethylacetamide

Product 1

HCID 143687603-(Heptyloxy)benzoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 2-liter three-necked flask were placed 100 g of methyl 3-hydroxybenzonate, 143 g of 1-bromoheptane, 140 g of potassium carbonate and 300 of N,N-dimethylacetamide (DMAc), and were vigorously stirred for 2 hours with a mechanical stirrer while the flask was heated in oil bath under reflux. After the obtained reaction mixture was cooled, it was poured into 1 l of water, and was extracted with ethyl acetate. Subsequently, the extract was dried under anhydrous sodium sulfate. After the extract was concentrated by removing the solvent in vacuo, the resultant residue was dissolved in 200 ml of methanol. Then, an aqueous solution (40 ml) containing potassium hydroxide of 8.4 g was dropwise added gradually to the ethanol solution and refluxed under heating for 1 hour. After the resultant reaction mixture was cooled, the precipitated crystals were filtered, and the resultant crystals were dissolved in 1.5 l of water. To the solution, 60 ml of concentrated hydrochloric acid was added. Then, the precipitated crystals were filtered in vacuo, washed with ice water and dried to obtain the above compound (2-4a) of 130 g (yield: 84%).

Workup

  1. customIn a 2-liter three-necked flask were placed
  2. temperaturewas heated in oil bath
  3. temperatureunder reflux
  4. customAfter the obtained reaction mixture
  5. temperaturewas cooled
  6. extractionwas extracted with ethyl acetate
  7. customSubsequently, the extract was dried under anhydrous sodium sulfate
  8. concentrationAfter the extract was concentrated
  9. customby removing the solvent in vacuo
  10. dissolutionthe resultant residue was dissolved in 200 ml of methanol
  11. additionThen, an aqueous solution (40 ml) containing potassium hydroxide of 8.4 g
  12. additionwas dropwise added gradually to the ethanol solution
  13. temperaturerefluxed
  14. temperatureunder heating for 1 hour
  15. customAfter the resultant reaction mixture
  16. temperaturewas cooled
  17. filtrationthe precipitated crystals were filtered
  18. dissolutionthe resultant crystals were dissolved in 1.5 l of water
  19. additionTo the solution, 60 ml of concentrated hydrochloric acid was added
  20. filtrationThen, the precipitated crystals were filtered in vacuo
  21. washwashed with ice water
  22. customdried

Sources & evidence

ORD record
ord-96cefef60a3043cf824e369571e3a877
Source dataset
uspto-grants-1996_05
Patent number
US05518783

Reaction notes

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