Toluene → HCID 53850864, compound

HRID 1464625Notes

Reaction equation

HRID 1464625 reaction equation
[F:1][C:2]1[CH2:7][C:6](F)([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](F)([C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:4][C:3]=1[F:26].CC(C1C=CC(O)=CC=1)(C1C=CC(O)=CC=1)C.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[F:1][C:2]1[CH2:7][CH:6]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]([C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:4][C:3]=1[F:26]

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 6623Bisphenol AHCID 11430Potassium CarbonateHCID 54405471HCID 54405471, compound

Product 1

HCID 53850864HCID 53850864, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

The synthesis of polycyclohexenepolyetherketone 28 was conducted in a three-neck flask equipped with a nitrogen inlet, Dean-Stark and condenser. A detailed synthetic procedure for its synthesis is as follows: The flask was charged with the monomer difluoro-4,5-difluoro-4,5-dibenzoylcyclohexene 3 (7.65 mmol, 2.48 g) and bisphenol (BPA) (7.65 mmol, 1.74 g) in N,N-dimethylacetamide (15 mL). Toluene (15 mL) was added, followed by anhydrous potassium carbonate (22.9 mmol, 3.2 g). The reaction mixture was then heated until toluene began to reflux. An optimum reflux temperature range was reached at 130° C. Toluene was periodically removed from the Dean-Stark trap to replace with dry toluene to ensure dehydration. The reaction mixture was maintained at 130° C. for 1-2 h at which point the viscosity increased enormously. The reaction mixture seemed to reach near completion or completion by the dramatic increase in viscosity and was then cooled, a few drops of acetic acid was added, and then diluted with toluene. The polymer solution was coagulated in a large amount of methanol, filtered, and washed with methanol. The white fibrous polymer 28 was redissolved in chloroform, hot filtered through Celite, reprecipitated into a large volume of methanol, filtered and dried in vacuo at 80° C. for 24 h. The yield was essentially quantitative.

Workup

  1. customThe synthesis of polycyclohexenepolyetherketone 28
  2. customwas conducted in a three-neck flask
  3. customequipped with a nitrogen inlet
  4. customA detailed synthetic procedure for its synthesis
  5. temperatureto reflux
  6. customwas reached at 130° C
  7. customToluene was periodically removed from the Dean-Stark trap
  8. temperatureincreased enormously
  9. temperaturedramatic increase in viscosity
  10. temperaturewas then cooled
  11. additiona few drops of acetic acid was added
  12. additiondiluted with toluene
  13. filtrationfiltered
  14. washwashed with methanol
  15. dissolutionThe white fibrous polymer 28 was redissolved in chloroform
  16. filtrationhot filtered through Celite
  17. customreprecipitated into a large volume of methanol
  18. filtrationfiltered
  19. customdried in vacuo at 80° C. for 24 h

Sources & evidence

ORD record
ord-acaaf18a0a544623a828b1f2f1e73765
Source dataset
uspto-grants-1994_04
Patent number
US05306789

Reaction notes

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