Water → HCID 14457497, compound

HRID 1458284Notes

Reaction equation

HRID 1458284 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). The mixture was refluxed with heating for 6 hours. The reaction solution, after water (150 ml) were added thereto, was extracted with chloroform. The extract was dried over sodium sulfite anhydride and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1), thereby yielding 13.00 g (90%) of methyl 4-geranyloxybenzoate.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 6 hours
  3. extractionwas extracted with chloroform
  4. dry with materialThe extract was dried over sodium sulfite anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-11ecc6804c3f49beb827298448f2f1d6
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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