Diphenyl Ether → Methanone, bis(4-phenoxyphenyl)-

HRID 1769933Notes

Reaction equation

HRID 1769933 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:17]([C:24]1[CH:32]=[CH:31][C:27](C(Cl)=O)=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(OC2C=CC=CC=2)C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3]>S(Cl)(Cl)=O.ClCCl.CCO>[O:17]([C:24]1[CH:25]=[CH:26][C:27]([C:12]([C:11]2[CH:15]=[CH:16][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)=[O:13])=[CH:31][CH:32]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 7583Diphenyl EtherHCID 741934-Phenoxybenzoyl chlorideHCID 751824-Phenoxybenzoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 84743Methanone, bis(4-phenoxyphenyl)-Yield 64.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

DPBO was prepared according to the following protocol: 4-phenoxybenzoic acid (2.5 g, 11.7 mmol) was refluxed in thionyl chloride (50 ml) for 3 hours. The resulting mixture was allowed to cool and the solvent removed in vacuo to recover 4-phenoxybenzoyl chloride as a pale yellow oil (2.72 g, Yield=100%, λ max=1760 cm-1). The 4-phenoxybenzoyl chloride (2.72 g, 11.7 mmol) in dichloromethane (20 ml) was added to diphenylether (1.99 g, 11.7 mmol) in dichloromethane (30 ml) followed by aluminium trichloride (1.56 g, 11.7 mmol) and the resulting mixture refluxed for 3 hours. The refluxed mixture was poured onto ice-water (approximately 100 ml) and the resulting layers separated. The aqueous layer was extracted with ether (2×100 ml extractions) and the combined organics dried, filtered and evaporated to recover the 4,4'-bis(phenoxy)benzophenone (2.76 g, yield=64%) as a colourless solid [melting point=130 to 132° C., λ max (EtOH)=291 nm (ε=2.3×104) and δH 6.9 to 7.9 (18H, M, Ar H)].

Workup

  1. customDPBO was prepared
  2. temperatureto cool
  3. customthe solvent removed in vacuo
  4. customto recover 4-phenoxybenzoyl chloride as a pale yellow oil (2.72 g, Yield=100%, λ max=1760 cm-1)
  5. temperaturethe resulting mixture refluxed for 3 hours
  6. additionThe refluxed mixture was poured onto ice-water (approximately 100 ml)
  7. customthe resulting layers separated
  8. extractionThe aqueous layer was extracted with ether (2×100 ml extractions)
  9. filtrationthe combined organics dried, filtered
  10. customevaporated

Sources & evidence

ORD record
ord-2cbcc4c3448241a6b33c728e8dd197f7
Source dataset
uspto-grants-1995_01
Patent number
US05384238

Reaction notes

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