4-Nitrobenzaldehyde → Fluoreneone

HRID 1461574Notes

Reaction equation

HRID 1461574 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.C(C1C=C(CCl)C2C3C(=CC(C(C)(C)C)=CC=3)CC=2C=1)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C1C=CC(C=O)=CC=1)([O-])=[O:57].[OH-].[K+]>O.N1C=CC=CC=1>[C:1]1(=[O:57])[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1

Participants

8

Reactant 5

HCID 5414-NitrobenzaldehydeHCID 6853FluoreneHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 13258138HCID 13258138, compound

Product 1

HCID 22281833FluoreneoneYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Into a 200 ml round-bottom flask, 5.0 g of a fluorene compound (m.p. 205.5°-207.5° C.) having the following structural formula ##STR8## which had been obtained by reacting 2,7-di-t-butyl-4-chloromethylfluorene with triphenylphosphine and then condensing the reaction product with 4-nitrobenzaldehyde, was introduced together with 0.3 g of potassium hydroxide and 100 ml of pyridine. The resulting mixture was stirred at room temperature for 20 hours in an air atmosphere. After completion of the reaction, 200 ml of water was added to the reaction mixture, and the reaction product was extracted with methylene chloride. The resulting organic layer was dried with Na2SO4 and the solvent was then removed by evaporation under reduced pressure. The residue was purified with a silica gel short column (methylene chloride/hexane = 2/1). Thereafter, the solvent was removed by evaporation under reduced pressure and the residue was recrystallized from a mixture of ethyl acetate and ethanol, thereby obtaining 1.7 g (yield 33%) of a fluorenone compound having the following structural formula as a yellow powder. The melting point of this compound was 223°-224° C. ##STR9##

Workup

  1. customthe following structural formula ##STR8## which had been obtained
  2. additionwas added to the reaction mixture
  3. extractionthe reaction product was extracted with methylene chloride
  4. dry with materialThe resulting organic layer was dried with Na2SO4
  5. customthe solvent was then removed by evaporation under reduced pressure
  6. customThe residue was purified with a silica gel short column (methylene chloride/hexane = 2/1)
  7. customThereafter, the solvent was removed by evaporation under reduced pressure
  8. customthe residue was recrystallized from a mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-73c8548c9a0c40d69eab89dfae9395d1
Source dataset
uspto-grants-1991_12
Patent number
US05075487

Reaction notes

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