Sodium Hydroxide → 5-Fluoro-[(3-fluorophenyloxy)methyl]benzoic acid

HRID 477791Notes

Reaction equation

HRID 477791 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:6]([CH:12]=1)[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:6]([CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14626278Ethyl 5-fluoro-2-[(3-fluorophenyloxy)methyl]benzoate

Product 1

HCID 146262795-Fluoro-[(3-fluorophenyloxy)methyl]benzoic acidYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 15 g of ethyl 5-fluoro-2-[(3-fluorophenyloxy)methyl]benzoate in 200 ml of ethanol is added 100 ml of 5% aqueous sodium hydroxide and the mixture is refluxed with heating for 1 hour. After cooling, the solvent is distilled off under reduced pressure and the residue is added with 300 ml of water and then with 10% hydrochloric acid to make the mixture acidic. The precipitated crystals are collected by filtration and dried to give 12 g of 5-fluoro-[(3-fluorophenyloxy)methyl]benzoic acid. Mass spectrum m/z: 264(M+).

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturewith heating for 1 hour
  3. temperatureAfter cooling
  4. distillationthe solvent is distilled off under reduced pressure
  5. additionthe residue is added with 300 ml of water
  6. filtrationThe precipitated crystals are collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-2ee5e64248d9445c952aac913af68abf
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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