Hydrochloric Acid → Diflunisal

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[C:13]([C:14]([O:16]C)=[O:15])[C:12]([OH:19])=[CH:11][CH:10]=1.[OH-].[Na+].Cl>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[C:13]([C:14]([OH:16])=[O:15])[C:12]([OH:19])=[CH:11][CH:10]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 491921Methyl 2',4'-difluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 3059Diflunisal

Procedure

The product of Step A above is suspended in 8.0 ml. of aqueous sodium hydroxide (5%) and refluxed for 30 minutes. The mixture is acidified with aqueous hydrochloric acid and extracted three times with 15.0 ml. of toluene. The combined toluene extracts are concentrated to afford 2.3 mmole of 5-(2,4-difluorophenyl)salicylic acid.