Potassium Hydroxide → Indeno[1,2-b]fluorene, 6,12-dihydro-

HRID 879910Notes

Reaction equation

HRID 879910 reaction equation
[CH:1]1[C:13]2[C:12](=O)[C:11]3[CH:10]=[C:9]4[C:15]5[C:20]([C:21](=O)[C:8]4=[CH:7][C:6]=3[C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:19][CH:18]=[CH:17][CH:16]=5.O.NN.[OH-].[K+]>C(O)COCCO.O>[CH:19]1[C:20]2[CH2:21][C:8]3[CH:7]=[C:6]4[C:5]5[C:13]([CH2:12][C:11]4=[CH:10][C:9]=3[C:15]=2[CH:16]=[CH:17][CH:18]=1)=[CH:1][CH:2]=[CH:3][CH:4]=5

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 144708915695-13-6

Product 1

HCID 15559295Indeno[1,2-b]fluorene, 6,12-dihydro-Yield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 17 g (60 mmol) of indeno[1,2-b]fluorene-6,12-dione, 18 g (600 mmol) of hydrazine monohydrate in 350 ml of diethylene glycol was stirred at 80° C. for 3 hours and then refluxed for 1 hour. The resulting mixture was cooled to room temperature, treated with a solution of 33 g (590 mmol) of KOH in 90 mL of water, and refluxed for 3 hours. The resulting mixture was poured into 800 ml of water, and the precipitate was filtered off, washed with water, and dried in air at room temperature to give product 13.1 g (51.6 mmol, 86%) as a yellow solid.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureThe resulting mixture was cooled to room temperature
  3. temperaturerefluxed for 3 hours
  4. filtrationthe precipitate was filtered off
  5. washwashed with water
  6. customdried in air at room temperature

Sources & evidence

ORD record
ord-52502c8dc97848e99e9e00a048241898
Source dataset
uspto-grants-2015_03
Patent number
US08993130B2

Reaction notes

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