Potassium Carbonate → HCID 67059839, compound

HRID 601458Notes

Reaction equation

HRID 601458 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH2:17][CH:18]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH3:19]>CC(C)=O>[CH3:19][C@@H:18]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH2:17][CH2:16][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 43282458-Bromo-2,6-dimethyloct-2-ene

Product 1

HCID 67059839HCID 67059839, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-cyanophenol (6.0 g, 50.0 mmol), potassium carbonate (27.6 g, 200 mmol) and citronellylbromide (13.15 g, 60.0 mmol) in acetone (200 mL) was heated under reflux for 24 hours. The solvent was evaporated and the residue was taken up with CH2Cl2 (60 mL×2) and the solution filtered. The solvent was evaporated and the resulting oil was purified by flash column chromatography over silica gel (EtOAc/hexanes 1:1) as eluant to give 4-[(3S)-3,7-dimethyl-6-octenyloxy]cyanobenzene (11.76 g, 45.7 mmol, 91.4% yield) as a white oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent was evaporated
  4. filtrationthe solution filtered
  5. customThe solvent was evaporated
  6. customthe resulting oil was purified by flash column chromatography over silica gel (EtOAc/hexanes 1:1) as eluant

Sources & evidence

ORD record
ord-67f4c1c99a004d5c846fb66a11ed4185
Source dataset
uspto-grants-2011_03
Patent number
US07902363B2

Reaction notes

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