Hydrochloric Acid → (4-Methoxyphenyl)(4-phenoxyphenyl)methanone

HRID 414752Notes

Reaction equation

HRID 414752 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].[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.Cl>ClCCl>[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([C:11]2[CH:10]=[CH:9][C:8]([O:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:13][CH:12]=2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 7583Diphenyl EtherHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19811057(4-Methoxyphenyl)(4-phenoxyphenyl)methanoneYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diphenyl oxide (52.2 g), 100 ml of dichloromethane, and 42.8 g of aluminum trichloride are added to a flask equipped with a mechanical stirrer, an addition funnel and a reflux condenser with a drying tube. 4-Methoxybenzoyl chloride (anisoyl chloride, 50 g) is added over 30 minutes. The mixture is stirred at ambient temperature for 2 days and then poured into 200 ml of 4M HCl. The organic layer is washed with 1M NaCl, dried with MgSO4, and evaporated. After bulb-to-bulb distillation at 215° C. using 0.3 mm Hg pressure, product is recrystallized from dry ethanol to give 69.1 g (78 percent yield) of the title compound, with a melting point of 118° C.-119° C.

Workup

  1. customequipped with a mechanical stirrer, an addition funnel and a reflux condenser with a drying tube
  2. washThe organic layer is washed with 1M NaCl
  3. dry with materialdried with MgSO4
  4. customevaporated
  5. distillationAfter bulb-to-bulb distillation at 215° C.
  6. customis recrystallized from dry ethanol

Sources & evidence

ORD record
ord-098dee7c4cd649d1a82ed9cc39ed77bd
Source dataset
uspto-grants-1988_12
Patent number
US04794155

Reaction notes

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