Acetone → 2-(p-Bromophenoxy)ethanol

HRID 263830Notes

Reaction equation

HRID 263830 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Br)[CH2:10][OH:11].C([O-])([O-])=O.[K+].[K+].CC(C)=O>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 78084-BromophenolHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 991682-(p-Bromophenoxy)ethanolYield 44.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reactor, 10.0 g of 4-bromophenol, 7.95 g of ethylene bromohydrin, 16.0 g of K2CO3, and 300 ml of acetone were charged, and stirred and refluxed for 50 hours to give a reaction solution. The reaction solution was poured into water, extracted with toluene, washed with water, and thereafter dried over sodium sulfate anhydride, and the solvent was evaporated and the residue was distilled under reduced pressure in GTO (glass tube oven) to give 5.55 g (Y., 44.3%) of 1-bromo-4-(2-hydroxyethoxy)benzene. GC; 96.8% b.p.; 100° C./0.1 mmHg (which was the prescribed temperature of GTO)

Workup

  1. temperaturerefluxed for 50 hours
  2. customto give a reaction solution
  3. extractionextracted with toluene
  4. washwashed with water
  5. dry with materialdried over sodium sulfate anhydride
  6. customthe solvent was evaporated
  7. distillationthe residue was distilled under reduced pressure in GTO (glass tube oven)

Sources & evidence

ORD record
ord-1dfc2e3ea3d44d62af1b49fe2e86566a
Source dataset
uspto-grants-1997_07
Patent number
US05645760

Reaction notes

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