Biphenyl → (4-nitrophenyl)-(4-phenylphenyl)methanone

HRID 1073072Notes

Reaction equation

HRID 1073072 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([C:22]2[CH:23]=[CH:24][C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:20][CH:21]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7095BiphenylHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 238626(4-nitrophenyl)-(4-phenylphenyl)methanone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Conditions

Temperature
50 °C

Procedure

A solution of 147 g (1.05 moles) of 4-nitrobenzoyl chloride in 250 ml of 1,2-dichloroethane and a solution of 154 g (1.0 mole) of biphenyl in 200 ml of 1,2-dichloroethane are added dropwise, in succession, to the suspension of 160 g (1.2 moles) of anhydrous aluminum chloride in 400 ml of 1,2-dichloroethane at 0° C. The mixture is allowed to reach room temperature, after which it is stirred for 2 hours at 50° C. and poured carefully onto ice water. The precipitate is filtered off under suction, washed thoroughly with water and recrystallized from ethanol to give 230 g (89% of theory) of brown crystals of melting point 174°-176° C.

Workup

  1. customto reach room temperature
  2. additionpoured carefully onto ice water
  3. filtrationThe precipitate is filtered off under suction
  4. washwashed thoroughly with water
  5. customrecrystallized from ethanol
  6. customto give 230 g (89% of theory) of brown crystals of melting point 174°-176° C.

Sources & evidence

ORD record
ord-e43a1563aef04e43b2b65e11c30dd8c4
Source dataset
uspto-grants-1990_11
Patent number
US04968676

Reaction notes

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