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

HRID 414753Notes

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

Participants

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

customequipped with a mechanical stirrer, a reflux condenser and an addition funnel
temperaturerefluxed for 4 hours
washthe organic layer is washed once with ammonium hydroxide and twice with water
dry with materialThe organic layer is dried with sodium bisulfate
customthe solvent is evaporated
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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