Hydrochloric Acid → 4-(Fluoromethyl)benzoic acid

HRID 1794249Notes

Reaction equation

HRID 1794249 reaction equation
[F:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CO>[F:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21866613Methyl 4-(fluoromethyl)benzoate

Product 1

HCID 139813684-(Fluoromethyl)benzoic acidYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 200 ml of methanol, 8.68 g of methyl 4-(fluoromethyl)benzoate was dissolved, and 77 ml of aqueous solution of 1 N sodium hydroxide was added dropwise with stirring and cooling. The mixture was then stirred for 3.5 hours at room temperature. After the mixture was acidified with 1 N hydrochloric acid, the precipitated crystals were collected by filtration, and the filtrate was concentrated. The precipitated crystals were combined with the residue obtained by concentrating the filtrate, and water was added thereto. The mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to provide 7.47 g of the objective compound as colorless crystals. M.p. 192–194° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was then stirred for 3.5 hours at room temperature
  3. filtrationthe precipitated crystals were collected by filtration
  4. concentrationthe filtrate was concentrated
  5. customobtained
  6. concentrationby concentrating the filtrate, and water
  7. additionwas added
  8. extractionThe mixture was extracted with ethyl acetate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1a0b090fc7af426090a5af10d5d0e770
Source dataset
uspto-grants-2006_04
Patent number
US07022723B2

Reaction notes

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