Phenol → Octyl phenyl ether

HRID 129652Notes

Reaction equation

HRID 129652 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[C:1]1([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 996PhenolHCID 81401-BromooctaneHCID 14797Potassium Hydroxide

Product 1

HCID 74558Octyl phenyl ether

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

44.8 g (or 0.477 mol) of phenol, 38.6 g (or 0.2 mol) of n-bromooctane, 6 g of tetrabutylammonium bromide, 26.8 g of potassium hydroxide, 100 ml of water and 100 ml of toluene were charged into a 500 ml, three-necked, round-bottom flask equipped with a mechanical stirrer, a thermometer and water-cooled reflux condenser. This medium was stirred and was then heated to reflux for 20 hours. The reaction mixture was then cooled to room temperature. The phases were settled and separated. The organic phase was washed with 100 ml of a 0.5N sodium hydroxide solution and then with five 100 ml fractions of water. It was then dried over magnesium sulfate and the solvent was then driven off under reduced pressure at a temperature of 85° C.

Workup

  1. customthree-necked, round-bottom flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperaturewas then heated
  4. temperatureto reflux for 20 hours
  5. customseparated
  6. washThe organic phase was washed with 100 ml of a 0.5N sodium hydroxide solution
  7. dry with materialIt was then dried over magnesium sulfate
  8. customwas then driven off under reduced pressure at a temperature of 85° C.

Sources & evidence

ORD record
ord-69cd5741ebdd4465bef6f975afb2e3ad
Source dataset
uspto-grants-1995_11
Patent number
US05468902

Reaction notes

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