3-Fluorophenol → 3-(3-Fluorophenoxy)propan-1-OL

HRID 440680

Reaction equation

HRID 440680 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[F:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[O:13][CH2:2][CH2:3][CH2:4][OH:5]

Participants

5

Reactant 3

HCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanol

Product 1

HCID 150860143-(3-Fluorophenoxy)propan-1-OLYield 82.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 24.3 grams (0.174 mole) of 3-bromopropanol, 20.6 grams (0.180 mole) of 3-fluorophenol, and 37.0 grams (0.270 mole) of potassium carbonate in 300 mL of acetone was heated at reflux for about 18 hours. The reaction mixture was then cooled and concentrated under reduced pressure to a residue, which was stirred with water and extracted with diethyl ether. The ether extract was washed with an aqueous 10% sodium hydroxide solution and then with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 24.5 grams of 3-(3-fluorophenoxy)propanol. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  3. temperatureThe reaction mixture was then cooled
  4. concentrationconcentrated under reduced pressure to a residue, which
  5. extractionextracted with diethyl ether
  6. extractionThe ether extract
  7. washwas washed with an aqueous 10% sodium hydroxide solution
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b71e9dc495c40c7a9792dc9cb5b7dd4
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Linked notes

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