Water → HCID 14457497, compound

HRID 2395245Notes

Reaction equation

HRID 2395245 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[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:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=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 14457497HCID 14457497, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 4-hydroxybenzoate (7.61 g) in acetone(80 ml) were added geranyl bromide (10.9 g) and potassium carbonate (13.8 g), and then the mixture was refluxed with heating for 6 hours. After the reaction, water (150 ml) was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate anhydride and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=9:1), thereby yielding 13.00 g of methyl 4-geranyloxybenzoate.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 6 hours
  3. additionwas added to the reaction mixture
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate anhydride
  6. concentrationconcentrated under a vacuum
  7. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8017c4bc297c455f8f6f3b9088ebfdab
Source dataset
uspto-grants-1998_09
Patent number
US05814634

Reaction notes

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