4-Fluorophenol → 3-(4-Fluorophenoxy)propionic acid

HRID 2051927Notes

Reaction equation

HRID 2051927 reaction equation
[H-].[Na+].Br[CH:4]([CH3:8])[C:5]([OH:7])=[O:6].[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>C(COC)OC>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:4]([CH3:8])[C:5]([OH:7])=[O:6])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 117292-Bromopropionic acidHCID 24758Sodium hydride

Product 1

HCID 38721403-(4-Fluorophenoxy)propionic acid

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To 83 g. of sodium hydride in 100 ml. of dry dimethoxyethane at 5° C. was added a solution of 15.3 g. of 2-bromopropionic acid in 50 ml. of dimethoxyethane and 10.5 g. of 4-fluorophenol in 50 ml. of dimethoxyethane. The slurry was heated to reflux for 6 hours, cooled and filtered. The crude solid was partitioned between methylenechloride and 1 N hydrochloric acid and this process repeated. The organic layer was dried and evaporated to 50 ml. The crystals were collected, washed with hexane and dried, m.p. 113°-115° C.

Workup

  1. temperatureThe slurry was heated
  2. temperatureto reflux for 6 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe crude solid was partitioned between methylenechloride and 1 N hydrochloric acid
  6. customThe organic layer was dried
  7. customevaporated to 50 ml
  8. customThe crystals were collected
  9. washwashed with hexane
  10. customdried

Sources & evidence

ORD record
ord-769bb8f8c131490b98116b67dfb4c7f7
Source dataset
uspto-grants-1980_01
Patent number
US04182776

Reaction notes

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