Hydrochloric Acid → [Propane-2,2-diyldi(4,1-phenylene)]bis[(4-fluorophenyl)methanone]

HRID 842255Notes

Reaction equation

HRID 842255 reaction equation
Cl[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19](Cl)=[O:20])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:6][CH:5]=1)=[O:3].[Cl-].[Al+3].[Cl-].[Cl-].Cl.[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:2]([C:4]2[CH:9]=[CH:8][C:7]([C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19](=[O:20])[C:31]4[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=4)=[CH:15][CH:14]=3)([CH3:12])[CH3:11])=[CH:6][CH:5]=2)=[O:3])=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10008FluorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 14401172HCID 14401172, compound

Product 1

HCID 22619077[Propane-2,2-diyldi(4,1-phenylene)]bis[(4-fluorophenyl)methanone]Yield 73%

Conditions

Temperature
55 °C

Procedure

A 250-ml, round-bottom flask was purged with argon and filled with 15.8653 g (0.0494 mol) of 2,2-bis-(4-chloroformylphenyl)propane (6HDAC) and 100 mL of fluorobenzene. To this solution was added with stirring 18.5 grams of anhydrous aluminum chloride in small portions over a 5-minute period. A small amount of heat was given off as evidenced by a slight rise in the temperature of the solution. The yellow reaction mixture was heated to 50-60° C. for 1.5 hours. The reaction progress was monitored by observing the HCl gas adsorption in a water trap. The reaction mixture was allowed to cool and then poured slowly into 700 ml of stirred, ice-cold 1M HCl. The lower organic layer was collected and concentrated to a light-red solid under reduced pressure. The solid was digested in 100 mL of ethanol for 12 hours and the resulting white solid was collected by filtration. Recrystallization from isopropyl alcohol yielded 15.8 g(73%) of 2,2-Bis-[4-(4-fluorobenzoyl)phenyl]propane (6HBFP), m.p. 167-168° C.

Workup

  1. customA 250-ml, round-bottom flask was purged with argon
  2. additionTo this solution was added
  3. temperatureA small amount of heat
  4. temperatureto cool
  5. additionpoured slowly into 700 ml
  6. customThe lower organic layer was collected
  7. concentrationconcentrated to a light-red solid under reduced pressure
  8. filtrationthe resulting white solid was collected by filtration
  9. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-d9aa8489b3544205a524ce2edf05fb82
Source dataset
uspto-grants-2002_04
Patent number
US06372877B1

Reaction notes

Loading…