Hydrochloric Acid → Methanone, [1,1'-biphenyl]-4-yl(3-methoxyphenyl)-

HRID 1408274Notes

Reaction equation

HRID 1408274 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[C:12]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[C:12]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:17]=[CH:16][C:15]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=2)=[O:10])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7095BiphenylHCID 74374m-Anisoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 6612595Methanone, [1,1'-biphenyl]-4-yl(3-methoxyphenyl)-Yield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an oven-dried flask placed under a nitrogen atmosphere, 3-anisoyl chloride (195 g) and biphenyl (190 g) were stirred in dichloromethane (1.4 L). The flask was placed in an ice bath and to it was added anhydrous aluminum chloride (172 g) in portions, each spaced 10 minutes apart. After the aluminum chloride addition was complete the reaction mixture was heated to reflux for 2 hours. After cooling to room temperature, the reaction mixture was slowly poured into a beaker containing a 10% aqueous solution of hydrochloric acid (1.5 L) and ice while stirring vigorously. A separatory funnel was used to separate the organic and aqueous layers. The recovered organic layer was then washed with deionized water three times with 1 liter each time, hereinafter designated as (3×1 L), dried over sodium sulfate and concentrated by rotary evaporation. Crystals formed while sitting overnight and were collected by vacuum filtration. A recrystallization was then performed by dissolving the crystals in a solution of 10% methanol/90% dichloromethane and subsequently removing nearly all of the solvent by rotary evaporation. Crystals formed while sitting overnight and were collected by vacuum filtration yielding 153 g of [1,1′-biphenyl]-4-yl(3-methoxyphenyl)methanone.

Workup

  1. customIn an oven-dried flask placed under a nitrogen atmosphere
  2. customThe flask was placed in an ice bath and to it
  3. customeach spaced 10 minutes
  4. temperaturewas heated
  5. temperatureto reflux for 2 hours
  6. additionthe reaction mixture was slowly poured into a beaker
  7. customA separatory funnel was used
  8. customto separate the organic and aqueous layers
  9. washThe recovered organic layer was then washed with deionized water three times with 1 liter each time
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated by rotary evaporation
  12. customCrystals formed
  13. filtrationwere collected by vacuum filtration
  14. customA recrystallization
  15. dissolutionby dissolving the crystals in a solution of 10% methanol/90% dichloromethane
  16. customsubsequently removing nearly all of the solvent
  17. customby rotary evaporation
  18. customCrystals formed
  19. waitwhile sitting overnight
  20. filtrationwere collected by vacuum filtration

Sources & evidence

ORD record
ord-ceea577fabdb43b3bdfc27ef64553300
Source dataset
uspto-grants-2014_12
Patent number
US08920928B2

Reaction notes

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