Hydrochloric Acid → 4-(9-Decen-1-yloxy)benzoic acid

HRID 2352588Notes

Reaction equation

HRID 2352588 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[I-].[Na+].[OH-:14].[K+].Cl.[CH3:17][C:18](=[O:21])[CH2:19][CH3:20]>>[CH2:2]([O:21][C:18]1[CH:17]=[CH:20][C:19]([C:18]([OH:21])=[O:14])=[CH:20][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 6569Methyl Ethyl KetoneHCID 14797Potassium Hydroxide2×HCID 1174513910-Chloro-1-decene

Product 1

HCID 148765254-(9-Decen-1-yloxy)benzoic acidYield 60%

Conditions

Temperature
80 °C

Procedure

10.0 g of 10-chloro-1-decene obtained in Example 1.(2) was iodized by reacting it with 25 g of sodium iodide in 2-butanone for 10 hours at 80° C. The resulting reaction mixture was then washed with water and dried, and the solvent was then removed. To the obtained iodide product were added 11.5 g of ethyl p-hydroxybenzoate and 9.6 g of potassium carbonate, and the mixture was refluxed in absolute ethanol for 15 hours. To the resulting reaction mixture was then added an aqueous potassium hydroxide solution containing 4.0 g of potassium hydroxide, and the mixture was further heated at 80° C. for 5 hours. After the reaction, the resulting reaction solution was made acid with hydrochloric acid and concentrated under reduced pressure. The resulting residue was suspended in water, and the insoluble material was corrected and dried to obtain 9.5 g of p-(9-decenyloxy)benozic acid. (Yield: 60%).

Workup

  1. customfor 10 hours
  2. customat 80° C
  3. customThe resulting reaction mixture
  4. washwas then washed with water
  5. customdried
  6. customthe solvent was then removed
  7. additionTo the obtained iodide product were added 11.5 g of ethyl p-hydroxybenzoate and 9.6 g of potassium carbonate
  8. temperaturethe mixture was refluxed in absolute ethanol for 15 hours
  9. customTo the resulting reaction mixture
  10. customAfter the reaction
  11. customthe resulting reaction solution
  12. concentrationconcentrated under reduced pressure
  13. customdried
  14. customto obtain 9.5 g of p-(9-decenyloxy)benozic acid

Sources & evidence

ORD record
ord-2cb7a94099da4bf5a212bb21e1295f7d
Source dataset
uspto-grants-1989_10
Patent number
US04877858

Reaction notes

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