Water → 4-Geranyloxybenzoic acid

HRID 1416211Notes

Reaction equation

HRID 1416211 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.[CH2:12](Br)/[CH:13]=[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])\[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:12]([O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)/[CH:13]=[C:14](/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])\[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Product 1

HCID 123615004-Geranyloxybenzoic acidYield 71.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 4-hydroxybenzoate (7.6 g), geranyl bromide (10.9 g), and potassium carbonate (13.8 g) were refluxed in acetone (80 ml) with stirring for 6 hours. The reaction mixture, with water added thereto, was extracted with chloroform. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was dissolved in methanol (50 ml) and the resulting mixture, with potassium hydroxide (3.9 g) and water (10 ml) added thereto, was stirred overnight at room temperature. The reaction mixture was neutralized with hydrochloric acid and then extracted with chloroform. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The resulting solid was recrystallized from n-hexane/ethanol to yield 9.8 g of the aimed compound.

Workup

  1. extractionwas extracted with chloroform
  2. dry with materialThe extract was dried over sodium sulfate anhydride
  3. concentrationconcentrated under a vacuum
  4. dissolutionThe residue was dissolved in methanol (50 ml)
  5. additionthe resulting mixture, with potassium hydroxide (3.9 g) and water (10 ml) added
  6. stirringwas stirred overnight at room temperature
  7. extractionextracted with chloroform
  8. dry with materialThe extract was dried over sodium sulfate anhydride
  9. concentrationconcentrated under a vacuum
  10. customThe resulting solid was recrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-44b26f419cdc44bfb0119537b9e32dc8
Source dataset
uspto-grants-1999_06
Patent number
US05912258

Reaction notes

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