Water → Octyl phenyl ether

HRID 703192Notes

Reaction equation

HRID 703192 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:9]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 81401-BromooctaneHCID 14797Potassium Hydroxide

Product 1

HCID 74558Octyl phenyl ether

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 224 grams (3 mols) of phenol in the form of a 88% aqueous solution, 193 grams (1 mol) of 1-bromooctane, 30 grams of tetra-n-butylammonium bromide, 224 grams (3 mols) of potassium hydroxide pellets, 500 ml of water and 500 ml of toluene was stirred under a nitrogen atmosphere while it was reflexing for a period of 16 hours. The reaction mixture was allowed to cool and the organic phase was washed with 500 ml, 0.5N sodium hydroxide to remove excess phenol. The toluene layer was washed with two 500 ml portions of water and the toluene was removed using a rotary evaporator. A quantitative yield of 98% pure octylphenyl ether was obtained based on gas chromotogrpahy and method of preparation.

Workup

  1. temperatureto cool
  2. washthe organic phase was washed with 500 ml, 0.5N sodium hydroxide
  3. customto remove excess phenol
  4. washThe toluene layer was washed with two 500 ml portions of water
  5. customthe toluene was removed
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-930587411a1e4dadbad56ab5f559a9c7
Source dataset
uspto-grants-1991_01
Patent number
US04981881

Reaction notes

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