Hydrochloric Acid → 1,1'-(9H-Fluorene-2,7-diyl)bis(4-chlorobutan-1-one)

HRID 441651Notes

Reaction equation

HRID 441651 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19].[Cl-:21].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[Cl:14][CH2:15][CH2:16][CH2:17][C:18]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:13](=[CH:1][C:2]([C:18](=[O:19])[CH2:17][CH2:16][CH2:15][Cl:21])=[CH:3][CH:4]=3)[CH2:12][C:11]=2[CH:10]=1)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6853FluoreneHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 131705491,1'-(9H-Fluorene-2,7-diyl)bis(4-chlorobutan-1-one)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 23.6 g (0.142 mole) of fluorene and 50.0 g (0.35 mole) of 4-chlorobutyryl chloride in 1500 ml of methylene chloride chilled to -20° C. is added 39.8 g (0.298 mole) of aluminum chloride with rapid stirring. The reaction mixture is refluxed four hours, stirred at room temperature for 16 hours, then poured onto ice/conc. HCl. The organic layer is separated, washed with saturated sodium bicarbonate solution and dried over magnesium sulfate. After filtration, the methylene chloride solution is evaporated to dryness and the solid residue recrystallized from acetone to yield 2,7-bis(4-chlorobutyryl)fluorene, M.P. 172°-175° C.

Workup

  1. temperatureThe reaction mixture is refluxed four hours
  2. additionpoured onto ice/conc
  3. customThe organic layer is separated
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe methylene chloride solution is evaporated to dryness
  8. customthe solid residue recrystallized from acetone

Sources & evidence

ORD record
ord-fe8b2b90041d419fb4908101b9cb3b4e
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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