Hydrochloric Acid → Diflunisal

HRID 223599Notes

Reaction equation

HRID 223599 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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 491921Methyl 2',4'-difluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 3059DiflunisalYield 98%

Procedure

The product of Step A. above is suspended in 80 ml. of aqueous sodium hydroxide (5%) and refluxed for 30 minutes. The mixture is acidified with aqueous hydrochloric acid and extracted three times with 150 ml. of toluene. The combined toluene extracts are concentrated and the 5-(2,4-difluorophenyl)salicylic acid is crystallized out. Filtration yields 29.4 mmole of final product, a 98% yield.

Workup

  1. extractionextracted three times with 150 ml
  2. concentrationThe combined toluene extracts are concentrated
  3. customthe 5-(2,4-difluorophenyl)salicylic acid is crystallized out
  4. filtrationFiltration

Sources & evidence

ORD record
ord-be052fcb8a054b4d9d1508ec3c1b2e81
Source dataset
uspto-grants-1982_10
Patent number
US04355174

Reaction notes

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