Acetonitrile → 1-((2-Ethylhexyl)oxy)-4-methoxybenzene

HRID 1796444Notes

Reaction equation

HRID 1796444 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22]Br)[CH3:20]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:22][CH:21]([CH2:19][CH3:20])[CH2:24][CH2:25][CH2:26][CH3:27])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromide

Product 1

HCID 33410051-((2-Ethylhexyl)oxy)-4-methoxybenzeneYield 79.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-methoxyphenol (100.0 g), dry potassium carbonate (166.7 g), acetonitrile (800 mL), and 2-ethylhexyl bromide (173.8 g) was stirred mechanically and heated at reflux for 4 days. The mixture was then allowed to cool to room temperature and was diluted with 1.5 L of deionized water, after which the organic phase was separated. The aqueous phase was extracted with hexane, and the combined organic layers were washed two times with a 1.0 moles/liter aqueous solution of NaOH and were then dried over MgSO4. The solvent was removed under reduced pressure to give an orange oil. The crude product was distilled under reduced pressure to give 152 g of a clear oil (bp 135–138° C. at 0.4 mmHg).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 days
  3. customafter which the organic phase was separated
  4. extractionThe aqueous phase was extracted with hexane
  5. washthe combined organic layers were washed two times with a 1.0 moles/liter aqueous solution of NaOH
  6. dry with materialwere then dried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customto give an orange oil
  9. distillationThe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-7f6fc9d52dd446018917b0059ffd35de
Source dataset
uspto-grants-2006_04
Patent number
US07030169B2

Reaction notes

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