Acetic Anhydride → 4-Fluorophenyl acetate

HRID 868527Notes

Reaction equation

HRID 868527 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([O-])(=[O:11])[CH3:10].[Na+].C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.O>[C:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 97324-FluorophenolHCID 516892Sodium BicarbonateHCID 517045Sodium Acetate

Product 1

HCID 1362534-Fluorophenyl acetateYield 128.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

4-Fluorophenol (112.1 g, 1.0 mole), sodium acetate (68.89 g, 0.74 mole) and acetic anhydride (107.6 g, 1.05 mole) were mixed in benzene (220 ml) with stirring and heated under reflux for 2 hours. After cooling, water (500 ml) and sodium bicarbonate (100 g, 1.19 mole) were added to the reaction mixture and the mixture was stirred. The mixture was allowed to stand to separate into layers and the aqueous layer was extracted with benzene (500 ml). The organic layers were combined, dried over anhydrous sodium sulfate and distilled to obtain the title compound (147 g, 95.4%), b.p. 84°-86° C./16 mmHg.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. stirringthe mixture was stirred
  5. customto separate into layers
  6. extractionthe aqueous layer was extracted with benzene (500 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled

Sources & evidence

ORD record
ord-575c62b5157a4f0286c0e82a73212921
Source dataset
uspto-grants-1988_10
Patent number
US04780471

Reaction notes

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