Diphenyl Ether → 4'-Phenoxyacetophenone

HRID 1632330Notes

Reaction equation

HRID 1632330 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15].F>>[O:7]([C:1]1[CH:2]=[CH:3][C:4]([C:14](=[O:16])[CH3:15])=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 7583Diphenyl Ether2×HCID 7918Acetic AnhydrideHCID 14917Hydrofluoric Acid

Product 1

HCID 2367834'-PhenoxyacetophenoneYield 99.25%

Conditions

Temperature
24 °C

Procedure

To a frozen solution of 1.70 g. (0.010 mole) diphenyl ether in 1.30 g. (0.012 mole; a 20 mole % excess) acetic anhydride, was added 3.0 ml anhydrous hydrogen fluoride (50% by weight of reactants). A magnetic stirrer was added and the reaction mixture was stirred magnetically and degassed several times while warming to 24° C. in air, and stirred for 18 hours at 24° C. The resultant red solution was poured into a plastic beaker and allowed to evaporate in an air stream/24° C., leaving a crystalline residue. This was crushed in ca 30 ml ice water, collected by filtration, partly air dried and further dried at 40° C. under a vacuum for about 2 hours, yielding 2.0 g. (94.2%) of nearly colorless crystals with a yellow tinge. Analysis showed only 0.73% unreacted diphenyl ether or 99.25% yield of p-phenoxyacetophenone by gas-liquid chromatography GLC. Thin layer chromatography (TLC) showed a very weak fast moving impurity spot corresponding to diphenyl ether while no trace of a slower moving spot which would correspond to a diacylation product was observed. The product had a melting point of 47°-50° C.

Workup

  1. additionA magnetic stirrer was added
  2. customdegassed several times
  3. stirringstirred for 18 hours at 24° C
  4. additionThe resultant red solution was poured into a plastic beaker
  5. customto evaporate in an air stream/24° C.
  6. customleaving a crystalline residue
  7. filtrationcollected by filtration, partly air
  8. customdried
  9. customfurther dried at 40° C. under a vacuum for about 2 hours
  10. customyielding 2.0 g

Sources & evidence

ORD record
ord-4f45535a575e46b4b12a2f27552354f3
Source dataset
uspto-grants-1984_10
Patent number
US04474990

Reaction notes

Loading…