Trimellitic anhydride → 9,9-Bis{4-(4-carboxy-phthalimido)phenyl}fluorene

HRID 1770296Notes

Reaction equation

HRID 1770296 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.[CH:28]1[C:33]([C:34]([OH:36])=[O:35])=[CH:32][C:31]2[C:37](O[C:40](=[O:41])[C:30]=2[CH:29]=1)=[O:38]>C1C(O)=CC=CC=1C>[C:34]([C:33]1[CH:32]=[C:31]2[C:37](=[O:38])[N:1]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4([C:21]5[CH:22]=[CH:23][C:24]([N:27]6[C:37](=[O:38])[C:31]7=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:28][CH:29]=[C:30]7[C:40]6=[O:41])=[CH:25][CH:26]=5)[C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=5[C:15]5[C:20]4=[CH:19][CH:18]=[CH:17][CH:16]=5)=[CH:6][CH:7]=3)[C:40](=[O:41])[C:30]2=[CH:29][CH:28]=1)([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 11089Trimellitic anhydrideHCID 6315524,4'-(9-Fluorenylidene)dianiline

Product 1

HCID 28325549,9-Bis{4-(4-carboxy-phthalimido)phenyl}fluoreneYield 88.7%

Reagents, catalysts & solvents 1

HCID 342M-CresolSolvent

Procedure

To a stirred mixture of 9,9-bis(4-aminophenyl)fluorene (13.9 g, 40 mmol) and 80 ml of m-cresol was added 1,2,4-benzenetricarboxylic anhydride (16.1 g, 84 mmol) over two minutes. The resulting mixture was stirred under gentle reflux (163°-170° C.) for three hours and then at ambient temperature for 16 hours. A pale yellow precipitate was filtered, washed with methanol, washed with toluene, and then dried in a vacuum oven at 100°-105° C. for 16 hours to provide the title compound as a pale yellow powder (24.7 g, 88.7% yield) that had a melting point of 328°-331° C. and a 1H NMR spectrum (DMSO d6) corresponding to δ8.39 (d,2H), 8.29 (br s, 2H), 8.05 (d, 2H), 8.00 (d, 2H), 7.61 (d, 2H), and 7.40 (m, 12H).

Workup

  1. temperatureunder gentle reflux (163°-170° C.) for three hours
  2. filtrationA pale yellow precipitate was filtered
  3. washwashed with methanol
  4. washwashed with toluene
  5. customdried in a vacuum oven at 100°-105° C. for 16 hours

Sources & evidence

ORD record
ord-e9a94300e8de49bd9eeda43437025b86
Source dataset
uspto-grants-1995_01
Patent number
US05386002

Reaction notes

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