Diethylene Glycol → 2-octyl-9H-fluorene

HRID 249213Notes

Reaction equation

HRID 249213 reaction equation
[C:1]([C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C:12]=2[CH:11]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O.NN.[OH-].[K+].C(O)COCCO>O>[CH2:1]([C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C:12]=2[CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 28016871-(9H-fluoren-2-yl)octan-1-one

Product 1

HCID 28016792-octyl-9H-fluoreneYield 80.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

In a 200 ml-three-necked flask, 6.00 g (20.5 mM) of 2-octanoylfluorene, 3.06 ml (50.4 mM) of hydrazine hydrate (80% aqueous solution), 4.20 g (63.6 mM) of potassium hydroxide and 60 ml of diethyleneglycol were placed, followed by heating to about 130° C. to dissolve the mixture. Then, the mixture was gradually heated to 210°-217° C., followed by stirring for 3 hours and 40 minutes under heating. After the reaction, the reaction mixture was cooled and poured into 250 ml of water to precipitate a crystal. The crystal was recovered by filtration and dissolved in toluene, followed by washing with water, drying with anhydrous sodium sulfate and distilling-off of the solvent. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/2) to obtain 4.58 g of 2-octylfluorene.

Workup

  1. dissolutionto dissolve the mixture
  2. temperatureThen, the mixture was gradually heated to 210°-217° C.
  3. temperatureunder heating
  4. customAfter the reaction
  5. temperaturethe reaction mixture was cooled
  6. customto precipitate a crystal
  7. filtrationThe crystal was recovered by filtration
  8. dissolutiondissolved in toluene
  9. washby washing with water
  10. dry with materialdrying with anhydrous sodium sulfate and distilling-off of the solvent
  11. customThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/2)

Sources & evidence

ORD record
ord-3b718af216a0420f8536f17b0af01296
Source dataset
uspto-grants-1993_05
Patent number
US05213709

Reaction notes

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