Hydrochloric Acid → 2,5-Dichloro-4'-phenoxybenzophenone

HRID 1600469Notes

Reaction equation

HRID 1600469 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:4]=1[C:5](Cl)=[O:6].[C:13]1([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:2][C:3]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:4]=1[C:5]([C:23]1[CH:24]=[CH:25][C:20]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:21][CH:22]=1)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7583Diphenyl EtherHCID 179452,5-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 120810592,5-Dichloro-4'-phenoxybenzophenoneYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a 22 L open-mouth round bottom flask fitted with a three-necked flange head, a mechanical stirrer, a nitrogen inlet and an outlet connected to an HCl scrubbing tower was added 2,5-dichlorobenzoylchloride (4500 g, 21.5 mol) and phenyl ether (5489 g, 32.3 mol). The solution was cooled in ice to 5° C. under stirring and aluminum chloride (3700 g, 27.8 mol) was added slowly. After about 300 g aluminum chloride was added, the solution started to foam violently. The rest was added carefully over about 10 min. On several occasions, the stirring had to be stopped to control the foaming. The temperature of the reaction mixture was about 35° C. after the addition. The mixture was then stirred for about 30 min. and poured into about 20 gallons of ice water. The large reddish mass was dissolved by adding about 12 L of methylene chloride and stirring. The organic layer was separated and the aqueous layer was extracted with some methylene chloride. After methylene chloride was removed from the combined organic layer by distillation, the residue was recrystallized twice from cyclohexane (2×10 L), washed with cooled hexane, air dried and then vacuum dried to afford 5387 g monomer (73%). The mother liquor was kept for later recovery of remaining product.

Workup

  1. customTo a 22 L open-mouth round bottom flask fitted with a three-necked flange head, a mechanical stirrer, a nitrogen inlet and an outlet
  2. additionThe rest was added carefully over about 10 min
  3. customwas about 35° C.
  4. additionafter the addition
  5. stirringThe mixture was then stirred for about 30 min.
  6. dissolutionThe large reddish mass was dissolved
  7. stirringstirring
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with some methylene chloride
  10. customAfter methylene chloride was removed from the combined organic layer by distillation
  11. customthe residue was recrystallized twice from cyclohexane (2×10 L)
  12. washwashed with cooled hexane, air
  13. customdried
  14. customvacuum dried

Sources & evidence

ORD record
ord-693a48ed000e4df3a576a90f19c5a1eb
Source dataset
uspto-grants-1999_11
Patent number
US05976437

Reaction notes

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