Pyridine → HCID 9500233, compound

HRID 1483778Notes

Reaction equation

HRID 1483778 reaction equation
C1C=C2C3[C:12]([C:13]([C:21]4[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=4)(C4C=CC(O)=CC=4)C2=CC=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.N1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH2:34]1COC[CH2:35]1>>[C:21]1([C:13]2[C:12]3[CH2:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:11]=3[CH:10]=[CH:9][CH:8]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 767169,9-Bis(4-hydroxyphenyl)fluorene

Product 1

HCID 9500233HCID 9500233, compoundYield 75%

Procedure

1,2,4-trimellitic anhydride acid chloride (120 mmole) was dissolved in 60 mL of anhydrous THF. Fluorene-9-bisphenol (60 mmole) and pyridine (14.5 mL) were dissolved in another 100 mL of anhydrous THF, and then slowly and dropwise added into the 1,2,4-trimellitic anhydride acid chloride solution under nitrogen, and then completely reacted at 40° C. for 12 hours. The reaction result was filtered to remove the salt thereof, and the solvent of the filtrate was removed by a rotary evaporator to obtain a solid. The solid was washed with n-hexane and re-crystallized from acetic anhydride two times to obtain a white solid (yield=75%). The 1H NMR spectrum of the white solid is listed below: 1H NMR (CDCl3, 400 MHz, ppm): 8.77 (s, 2H), 8.69 (d, 2H), 8.14 (d, 2H), 7.82 (d, 2H), 7.43 (m, 4H). The above-mentioned reaction is represented as:

Workup

  1. customcompletely reacted at 40° C. for 12 hours
  2. customThe reaction result
  3. filtrationwas filtered
  4. customto remove the salt
  5. customthe solvent of the filtrate was removed by a rotary evaporator
  6. customto obtain a solid
  7. washThe solid was washed with n-hexane
  8. customre-crystallized from acetic anhydride two times

Sources & evidence

ORD record
ord-2928fed4a65c41488e432424af314e28
Source dataset
uspto-grants-2016_08
Patent number
US09416229B2

Reaction notes

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