Water → Methyl 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}acetate

HRID 1393848Notes

Reaction equation

HRID 1393848 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])\[CH3:22].O>CC(C)=O>[CH3:22][C:21]([CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])=[CH:20][CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Product 1

HCID 69306599Methyl 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}acetateYield 92.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 4-hydroxyphenylacetate (6.00 g, 36.11 mmol) was dissolved in acetone (90 ml), and then potassium carbonate (9.98 g, 72.22 mmol) and geranyl bromide(14.34 ml, 72.22 mmol) were added thereto. After being refluxed for 4 hours, the mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride water and saturated brine successively, and dried over MgSO4. The solvent was evaporated out and the obtained residue was purified by silica gel column chromatography (5% ethyl acetate/hexane), to give methyl 2-{4-[(3,7-dimethyl-2,6-octadienyl)oxy]phenyl}acetate (10.07 g, 92%).

Workup

  1. temperatureAfter being refluxed for 4 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated ammonium chloride water and saturated brine successively
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated out
  6. customthe obtained residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-08dd9b8c067f4662880f983f1bca2556
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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