Phenol → 4-Chlorobutyl phenyl ether

HRID 1082137Notes

Reaction equation

HRID 1082137 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14]Cl>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:10][CH2:11][CH2:12][CH2:13][CH2:14][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 80591,4-DichlorobutaneHCID 14798Sodium Hydroxide

Product 1

HCID 758574-Chlorobutyl phenyl etherYield 77%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

A two phase mixture of phenol (5 g, 53 mmol), 1,4-dichlorobutane (30 ml), tetrabutylammonium hydrogen sulphate (0.3 g, 1 mmol), and sodium hydroxide solution (25 ml, 6M) was refluxed for 3 h. The organic layer was separated, dried (MgSO4), and concentrated in vacuo. The residues were purified by flash chromatography (silica (Merck 15111); eluant:petrol) to give the product as a colourless viscous oil (7.57 g 77%) bp 250° C. at 0.2 mm Hg.

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residues were purified by flash chromatography (silica (Merck 15111); eluant:petrol)

Sources & evidence

ORD record
ord-d5be852087e444f7959382c727968603
Source dataset
uspto-grants-1996_12
Patent number
US05589500

Reaction notes

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