Water → 4-Geranyloxybenzoic acid

HRID 850394Notes

Reaction equation

HRID 850394 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][CH:3]=1.[CH2:13](Br)/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([OH:8])=[O:7])=[CH:11][CH:12]=1)/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Product 1

HCID 123615004-Geranyloxybenzoic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-hydroxybenzoate (16.6 g), geranyl bromide (23.9 g), and potassium carbonate (27.6 g) were refluxed in acetone (200 ml) with stirring for 1 hour . The reaction mixture, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride. and then concentrated under a vacuum. To the residue dissolved in ethanol (150 ml) were added sodium hydroxide (3.90 g) and water(50 ml) and the mixture was refluxed with stirring for 1 hour. After being concentrated under a vacuum, the reaction mixture was acidified with hydrochloric acid and then extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride and then was concentrated under a vacuum. The resulting solid was recrystallized from n-hexane/ethyl acetate mixed solution, thereby yielding 22.3 g of the aimed compound.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate anhydride
  3. concentrationand then concentrated under a vacuum
  4. dissolutionTo the residue dissolved in ethanol (150 ml)
  5. additionwere added sodium hydroxide (3.90 g) and water(50 ml)
  6. temperaturethe mixture was refluxed
  7. stirringwith stirring for 1 hour
  8. concentrationAfter being concentrated under a vacuum
  9. extractionextracted with ethyl acetate
  10. dry with materialThe extract was dried over sodium sulfate anhydride
  11. concentrationwas concentrated under a vacuum
  12. customThe resulting solid was recrystallized from n-hexane/ethyl acetate mixed solution

Sources & evidence

ORD record
ord-72cc9cd48e4946798b297b9c8ed34d67
Source dataset
uspto-grants-2000_01
Patent number
US06017937

Reaction notes

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