Acetic Anhydride → Flufenisal

HRID 442275Notes

Reaction equation

HRID 442275 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:18](OC(=O)C)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 27826944'-Fluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylic acid

Product 1

HCID 31185Flufenisal

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3.0 grams of 2-hydroxy-5-(4'-fluorophenyl)-benzoic acid in 12 ml. of pyridine and 8 ml. of acetic anhydride is heated on a steam bath for 20 minutes. The mixture is then poured onto ice and the product extracted with methylene chloride. The methylene chloride solution is dried and then evaporated. The residue is recrystallized from benzene to yield 2-acetoxy 5-(4'-fluorophenyl)-benzoic acid (m.p. 134° - 137° C.).

Workup

  1. additionThe mixture is then poured onto ice
  2. extractionthe product extracted with methylene chloride
  3. dry with materialThe methylene chloride solution is dried
  4. customevaporated
  5. customThe residue is recrystallized from benzene

Sources & evidence

ORD record
ord-7ba937c926934c758493afec3417b601
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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