P-Xylene → Fluorene

HRID 1576960Notes

Reaction equation

HRID 1576960 reaction equation
C[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1>C(O)C.C(O)COCCO.NN.[Na].[OH-].[K+]>[CH:7]1[C:6]2[CH2:5][C:6]3[C:5](=[CH:4][CH:3]=[CH:2][CH:7]=3)[C:8]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 1

HCID 7809P-Xylene

Product 1

HCID 6853Fluorene

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 8117Diethylene GlycolSolventHCID 9321HydrazineSolventHCID 14797Potassium HydroxideSolventHCID 5360545SodiumSolvent

Procedure

The 2,7-bis-basic alkanes (IX) are prepared from the corresponding 2,7-bis-basic ketones (II) via the general reaction conditions of the Wolff-Kishner reduction, utilizing hydrazine and a base catalyst in an organic solvent. The desired product can be obtained by the direct reduction of the corresponding ketone, or the reduction may proceed in a stepwise fashion by the isolation of the hydrazone intermediate which is then subsequently reduced. In general the 2,7-bis-basic ketones are dissolved in an organic solvent such as ethanol, diethylene glycol or p-xylene to which hydrazine and sodium or potassium hydroxide or alkoxide is added. The reaction mixture is heated from about 140° to about 180°C for a period of from 12 to 48 hours to form the desired 2,7-bis-basic alkanes of fluorene.

Workup

  1. additionis added
  2. temperatureThe reaction mixture is heated from about 140° to about 180°C for a period of from 12 to 48 hours

Sources & evidence

ORD record
ord-1a411f98dedd45a2b3fdf756be6ac0a8
Source dataset
uspto-grants-1976_09
Patent number
US03983124

Reaction notes

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