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

HRID 1653615Notes

Reaction equation

HRID 1653615 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) Chloride

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 a HCl scrubbing tower, is added 2,5-dichlorobenzoic chloride (4500 g, 21.5 mol) and phenyl ether (5489 g, 32.3 mol). The solution is cooled in ice to 5° C. under stirring, and aluminum chloride (3700 g, 27.8 mol) is added slowly, over a period of about 10 minutes. The temperature of the reaction mixture is about 35° C. after the addition. The mixture is then stirred for about 30 minutes and poured into about 20 gallons of ice water. The large reddish mass is dissolved by adding about 12 L of methylene chloride and stirring. The organic layer is separated and the aqueous layer is extracted with some methylene chloride. After methylene chloride is removed from the combined organic layer by distillation, the residue is 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 is 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. customis about 35° C.
  3. additionafter the addition
  4. stirringThe mixture is then stirred for about 30 minutes
  5. dissolutionThe large reddish mass is dissolved
  6. stirringstirring
  7. customThe organic layer is separated
  8. extractionthe aqueous layer is extracted with some methylene chloride
  9. customAfter methylene chloride is removed from the combined organic layer by distillation
  10. customthe residue is recrystallized twice from cyclohexane (2×10 L)
  11. washwashed with cooled hexane, air
  12. customdried
  13. customvacuum dried

Sources & evidence

ORD record
ord-3ddf9063c201453fac84204e221a006a
Source dataset
uspto-grants-1995_04
Patent number
US05403675

Reaction notes

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