Hydrochloric Acid → 1,6-Bis(4-fluorophenyl)hexane-1,6-dione

HRID 1885658Notes

Reaction equation

HRID 1885658 reaction equation
[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6](Cl)=[O:7].[Cl-].[Al+3].[Cl-].[Cl-].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:1]([CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)=[O:9])=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10008FluorobenzeneHCID 61034Adipoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125474961,6-Bis(4-fluorophenyl)hexane-1,6-dioneYield 76%

Procedure

Adipoyl chloride (45.8 g, 0.25 mol) was added over a 30-45 minute period to a mechanically stirred suspension of aluminum chloride (83.3 g, 0.625 mol) in fluorobenzene (235 ml, 2.5 mol) maintained at 5°-10° C. The yellow slurry was allowed to warm to room temperature and was stirred overnight. The reaction mixture was poured onto approximately 1000 g of ice containing 100 ml of concentrated hydrochloric acid. The resulting suspension was separated by decantation and washed several times with water. The organic layer was distilled to remove excess fluorobenzene and the solid residue collected by filtration, washed with water, and dried at 110° C. The crude solid was recrystallized from approximately 1000 ml of toluene to afford 57.0 g (76% yield) of 1,4-bis(4-fluorobenzoyl) butane; mp 165°-167° C.; 'H NMR (CDCl3) δ1.2-2.1 (m, 4H, CH2), 3.00 (t, 4H, O=CCH2 , J=7.0 Hz), 7.0-8.2 (m, 8H, aromatic). Anal. Calcd. for C18H16F2O2 : C, 71.51%; H, 5.33%; F, 12.57%. Found: C, 71.68%; H, 5.38%; F, 12.78%.

Workup

  1. temperaturemaintained at 5°-10° C
  2. customThe resulting suspension was separated by decantation
  3. washwashed several times with water
  4. distillationThe organic layer was distilled
  5. customto remove excess fluorobenzene
  6. filtrationthe solid residue collected by filtration
  7. washwashed with water
  8. customdried at 110° C
  9. customThe crude solid was recrystallized from approximately 1000 ml of toluene

Sources & evidence

ORD record
ord-a38e4853e2d048ef9e4c7a0d1f1c098d
Source dataset
uspto-grants-1992_09
Patent number
US05145937

Reaction notes

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