Hydrochloric Acid → 3-(3-Fluorophenoxy)propanoic acid

HRID 429055

Reaction equation

HRID 429055 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.Br[CH2:12][CH2:13][C:14]([OH:16])=[O:15].Cl>O>[F:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97433-FluorophenolHCID 115533-Bromopropionic acidHCID 14798Sodium Hydroxide

Product 1

HCID 150860153-(3-Fluorophenoxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (6.7 gm, 167 mmol) in water (20 mL) was added slowly to a neat mixture of 3-fluorophenol (8.9 gm, 79.5 mmol) and 3-bromopropionic acid (12.26 gm,80 mmol) as the reaction became exothermic. The mixture was refluxed gently for two hours and then allowed to cool and become semi-solid. Water was added to dissolve the semi-solid and then was acidified with concentrated HCl. The product was extracted into diethyl ether and the ethereal extract was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was slurried in 4:1 hexanetbenzene to give crystalline 3-(3-fluorophenoxy) propionic acid. m.p.: 90-91° C.

Workup

  1. temperatureThe mixture was refluxed gently for two hours
  2. temperatureto cool
  3. dissolutionto dissolve the semi-solid
  4. extractionThe product was extracted into diethyl ether
  5. extractionthe ethereal extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-81a6494de2414bae9f8d97f8e2860d52
Source dataset
uspto-grants-2001_11
Patent number
US06316437B1

Linked notes

Loading…