4-Hydroxyphthalic acid → 9,9-Bis{4-(4-hydroxy-phthalimido)phenyl}fluorene

HRID 129952Notes

Reaction equation

HRID 129952 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([C:34]3[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=3)[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=1>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]2[C:11](=[O:13])[N:14]([C:15]3[CH:16]=[CH:17][C:18]([C:21]4([C:34]5[CH:35]=[CH:36][C:37]([N:40]6[C:11](=[O:13])[C:4]7=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=[C:5]7[C:6]6=[O:8])=[CH:38][CH:39]=5)[C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=5[C:28]5[C:33]4=[CH:32][CH:31]=[CH:30][CH:29]=5)=[CH:19][CH:20]=3)[C:6](=[O:8])[C:5]2=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 118814-Hydroxyphthalic acidHCID 6315524,4'-(9-Fluorenylidene)dianiline

Product 1

HCID 200959569,9-Bis{4-(4-hydroxy-phthalimido)phenyl}fluoreneYield 53.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4-hydroxyphthalic acid (4.0 g, 22 mmol), 9,9-bis(4-aminophenyl)fluorene (3.5 g, 10 mmol), and 40 ml of acetic acid was stirred and heated under reflux for 48 hours. After cooling to room temperature, the precipitate was collected by filtration and washed with acetic acid (2×25 ml) to provide the title compound as a colorless powder having a melting point greater than 300° C. (3.4 g, 53.1% yield). The nuclear magnetic resonance and infrared spectrum were consistent with the structure.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 hours
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with acetic acid (2×25 ml)

Sources & evidence

ORD record
ord-0d0ee15306b84bccbff4bb1e099f8ae4
Source dataset
uspto-grants-1995_11
Patent number
US05470987

Reaction notes

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