Phenol → HCID 20455137, compound

HRID 1702147Notes

Reaction equation

HRID 1702147 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>C1(=O)CCCC1>[Br:14][CH2:15][CH2:16][CH:17]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:18]

Participants

5

Procedure

A mixture of 329 g of phenol, 484 g of dry potassium carbonate, 756 g of 1,4-dibromobutane and 1,000 ml of cyclopentanone is refluxed for 24 hours, whilst stirring. The solid constituents are filtered off and the filtrate is then concentrated under reduced pressure; the oily residue is taken up in 1,500 ml of methylene chloride and this solution is extracted ten times with 200 ml of 15 percent strength aqueous sodium hydroxide solution at a time. The organic phase is then extracted twice with 300 ml of water at a time, dried over magnesium sulate, filtered and concentrated under reduced pressure. Distillation of the residue gives, at 92°-98° C./0.4 mbar, 395 g of colorless 1-bromo-3-phenoxybutane, which solidifies in the receiver; melting point 33°-36° C.

Workup

  1. temperatureis refluxed for 24 hours
  2. filtrationThe solid constituents are filtered off
  3. concentrationthe filtrate is then concentrated under reduced pressure
  4. extractionthis solution is extracted ten times with 200 ml of 15 percent strength aqueous sodium hydroxide solution at a time
  5. extractionThe organic phase is then extracted twice with 300 ml of water at a time
  6. dry with materialdried over magnesium sulate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. distillationDistillation of the residue

Sources & evidence

ORD record
ord-f1779171f0cc4a5cb76179387a3e1abf
Source dataset
uspto-grants-1983_04
Patent number
US04380546

Reaction notes

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