Hydrochloric Acid → 3-(3-Fluorophenoxy)butyric Acid

HRID 1722044Notes

Reaction equation

HRID 1722044 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[C:11]1(=[O:16])[O:15][CH:13]([CH3:14])[CH2:12]1.Cl>O>[F:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH:13]([CH3:14])[CH2:12][C:11]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97433-FluorophenolHCID 14798Sodium HydroxideHCID 18303beta-BUTYROLACTONE

Product 1

HCID 147733803-(3-Fluorophenoxy)butyric Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 35.72 g (0.893 mol) sodium hydroxide in 357 ml water was added 100 g (0.893 mol) 3-fluorophenol. The reaction was heated to reflux and to the gently refluxing solution was added 72.8 ml (0.893 mol) beta-butyrolactone dropwise over 1.5 hours. The reaction was cooled to 23° C. and the pH brought to 2 with concentrated hydrochloric acid. The reaction was extracted with 300 ml diethyl ether and the ether layer was separated, washed with brine and then extracted with 3×200 ml saturated sodium bicarbonate. The combined bicarbonate layers were washed with 200 ml diethyl ether, acidified with 50 ml concentrated hydrochloric acid and extracted with 300 ml diethyl ether. The latter ether extract was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give the product as a red oil, 31.6 g (17.9%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux and to the gently refluxing solution
  3. extractionThe reaction was extracted with 300 ml diethyl ether
  4. customthe ether layer was separated
  5. washwashed with brine
  6. extractionextracted with 3×200 ml saturated sodium bicarbonate
  7. washThe combined bicarbonate layers were washed with 200 ml diethyl ether
  8. extractionextracted with 300 ml diethyl ether
  9. extractionThe latter ether extract
  10. washwas washed with brine
  11. dry with materialdried over magnesium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-582b94faa3954384a06e3f6c2d617b72
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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