Water → Octyl phenyl ether

HRID 1638966Notes

Reaction equation

HRID 1638966 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-4f126d1f3d0e4b1d8930deaad6ef8e8c
Source dataset
uspto-grants-1989_11
Patent number
US04882201

Reaction notes

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