Potassium Carbonate → 6-[(3,7-Dimethylocta-2,6-dien-1-YL)oxy]-2,3-dihydro-1-benzofuran

HRID 1414804Notes

Reaction equation

HRID 1414804 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.[CH2:11](Br)/[CH:12]=[C:13](/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])\[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:14][C:13]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:12][CH2:11][O:1][C:2]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-HCID 122365402,3-Dihydro-1-benzofuran-6-ol

Product 1

HCID 541798386-[(3,7-Dimethylocta-2,6-dien-1-YL)oxy]-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 27.7 g. of 6-hydroxy-2,3-dihydrobenzofuran, 52.1 g. of geranyl bromide and 41.4 g. of anhydrous powdered potassium carbonate in 200 ml. of methyl ethyl ketone is heated under reflux with stirring for 70 hours. The cooled reaction mixture is filtered, the residual potassium carbonate washed with acetone and the filtrate evaporated. By chromatography on silica gel with hexane/diethyl ether (4:1 parts by volume) there is obtained pure 6-[(3,7-dimethyl-2,6-octadienyl)-oxy]-2,3-dihydrobenzofuran of boiling poiint 130° C./0.001 mmHg.; nD20 = 1.5414.

Workup

  1. additionA mixture of 27.7 g
  2. temperatureunder reflux
  3. customThe cooled reaction mixture
  4. filtrationis filtered
  5. washthe residual potassium carbonate washed with acetone
  6. customthe filtrate evaporated

Sources & evidence

ORD record
ord-d39bfd713b454ba1bcdb987a9a4e5468
Source dataset
uspto-grants-1977_01
Patent number
US04002647

Reaction notes

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