Hydrochloric Acid → 1,8-Bis(4-fluorophenyl)octane-1,8-dione

HRID 1885659

Reaction equation

HRID 1885659 reaction equation
[C:1](Cl)(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](Cl)=[O:9].[Cl-].[Al+3].[Cl-].[Cl-].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8](=[O:9])[C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)=[O:11])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10008FluorobenzeneHCID 534653Octanedioyl dichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18847471,8-Bis(4-fluorophenyl)octane-1,8-dioneYield 67.3%

Procedure

Suberoyl chloride (40.8 g, 0.1933 mol) was added over a 30-45 minute period to a mechanically stirred suspension of aluminum chloride (64.4 g, 0.483 mol) in fluorobenzene (181 ml, 1.93 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 75 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 100° C. The crude solid was recrystallized from approximately 500 ml of toluene to afford 43.0 g (67% yield) of 1,6-bis(4-fluorobenzoyl)hexane; mp 123°-124° C.; 'H NMR (CDCl3) δ1.0-2.1 (m, 8H, CH2), 2.97 (t, 4H, O=CCH2, J=7.0 Hz), 6.9-8.3 (m, 8H, aromatic). Anal. Calcd. for C20H20F2O2 : C, 72.71%; H, 6.10%; F, 11.50%. Found: C, 72.50%; H, 5.86%; F, 11.19%.

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 100° C
  9. customThe crude solid was recrystallized from approximately 500 ml of toluene

Sources & evidence

ORD record
ord-cbbcfbf5ccb0474c9c1ec92e26b65d97
Source dataset
uspto-grants-1992_09
Patent number
US05145937

Linked notes

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