Isopropanol → 1-bromo-4-propoxybenzene

HRID 612596Notes

Reaction equation

HRID 612596 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:15](O)([CH3:17])[CH3:16]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][CH2:15][CH3:17])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 27341981-bromo-4-propoxybenzeneYield 60%

Procedure

Prepare a solution of 4-bromo-phenol (17.30 g, 0.10 mol) and potassium carbonate (13.80 g, 0.1 mole) in isopropanol (175 mL). Heat the resulting mixture at reflux and stir overnight. Cool to ambient temperature, filter and condense the filtrate on a rotary evaporator. Dissolve the residual oil in ethyl acetate (250 mL) and extract twice with 5% sodium hydroxide (100 mL), separate and wash with brine. Kugelrohr distillation at 100°-120°, 0.05 mm, gives the title compound (12.86 g, 60%) as a clear liquid.

Workup

  1. temperatureHeat the resulting mixture
  2. temperatureat reflux
  3. filtrationfilter
  4. customcondense the filtrate
  5. customon a rotary evaporator
  6. dissolutionDissolve the residual oil in ethyl acetate (250 mL)
  7. extractionextract twice with 5% sodium hydroxide (100 mL)
  8. customseparate
  9. washwash with brine
  10. distillationKugelrohr distillation at 100°-120°

Sources & evidence

ORD record
ord-2243f16082e944429680783b4475a7a0
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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