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Hydrochloric Acid → Methanone, 1,3-phenylenebis[(4-phenoxyphenyl)-

HRID 414753
Notes
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Reaction equation

HRID 414753 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.[Cl-].[Cl-].[Cl-].[Al+3].[C:18](Cl)(=[O:28])[C:19]1[CH:27]=[CH:26][CH:25]=[C:21]([C:22](Cl)=[O:23])[CH:20]=1.Cl>ClCCl>[O:7]([C:1]1[CH:2]=[CH:3][C:4]([C:18]([C:19]2[CH:27]=[CH:26][CH:25]=[C:21]([C:22](=[O:23])[C:11]3[CH:12]=[CH:13][C:8]([O:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:9][CH:10]=3)[CH:20]=2)=[O:28])=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7451Isophthaloyl chlorideHCID 7583Diphenyl EtherHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11070706Methanone, 1,3-phenylenebis[(4-phenoxyphenyl)-Yield 61%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
-60 °C

Procedure

Diphenyl oxide (51 g), 100 ml of dichloromethane and 13.3 g of aluminum trichloride are placed in a flask equipped with a mechanical stirrer, a reflux condenser and an addition funnel. After cooling the flask to -60° C., 10.15 g of isophthaloyl chloride is added over a 30-minute period. The reaction is stirred at 25° C. for 72 hours and refluxed for 4 hours. The reaction mixture is poured into 100 ml of 1M hydrochloric acid and the organic layer is washed once with ammonium hydroxide and twice with water. The organic layer is dried with sodium bisulfate and the solvent is evaporated. The product is recrystallized from methylethyl ketone, yielding 14.3 g (61 percent yield) of the title compound.

Workup

  1. customequipped with a mechanical stirrer, a reflux condenser and an addition funnel
  2. temperaturerefluxed for 4 hours
  3. washthe organic layer is washed once with ammonium hydroxide and twice with water
  4. dry with materialThe organic layer is dried with sodium bisulfate
  5. customthe solvent is evaporated
  6. customThe product is recrystallized from methylethyl ketone

Sources & evidence

ORD record
ord-3662bedfbbfa4b4dadd802fd3f06f835
Source dataset
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04794155

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes