1-Bromopropane → 3-(4-Propoxyphenyl)propan-1-ol

HRID 1169498Notes

Reaction equation

HRID 1169498 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1)[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 219387043-(4-Propoxyphenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-(4-hydroxyphenyl)-1-propanol (1.33 g), 1-bromopropane (1.2 ml) and potassium carbonate (2.25 g) and acetone (100 ml) was heated at reflux for 2 days. After concentration under reduced pressure, the residue was mixed with water and was extracted with ethyl acetate. The organic layer was washed with a 1 N aqueous solution of sodium hydroxide and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 3-(4-propoxyphenyl)-1-propanol (1.61 g) as a colorless oily substance.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. concentrationAfter concentration under reduced pressure
  4. additionthe residue was mixed with water
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with a 1 N aqueous solution of sodium hydroxide
  7. dry with materialan aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate
  8. customThe resulting organic layer was evaporated under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-40e2b83a5f174d438df3ccbc959b8ed0
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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