1-Naphthol → HCID 131717523, compound

HRID 1885662Notes

Reaction equation

HRID 1885662 reaction equation
F[C:2]1[C:7]([C:8]2[C:13]([F:14])=[C:12]([F:15])[C:11](F)=[C:10]([F:17])[C:9]=2[F:18])=[C:6]([F:19])[C:5]([F:20])=[C:4]([F:21])[C:3]=1[F:22].[C:23]1([OH:33])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.[C:34](=[O:37])([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[C:23]1([O:33][C:11]2([O:37][C:34]3[C:2]4[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:8]=[CH:9][CH:10]=3)[C:10]([F:17])=[C:9]([F:18])[C:8]([C:7]3[CH:2]=[C:3]([F:22])[C:4]([F:21])=[C:5]([F:20])[C:6]=3[F:19])=[C:13]([F:14])[CH:12]2[F:15])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 67949Decafluorobiphenyl

Product 1

HCID 131717523HCID 131717523, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

The monomer 4,4,-bis(1-naphthoxy)octafluorobiphenyl (8FNE) was prepared by the following procedure. A 100 mL round bottom flask was charged with decafluorobiphenyl (3.01 g, 0.0090 mole), 1-naphthol (2.60 g, 0.0181 mole), potassium carbonate (2.95 g, 0.0218 mole), and DMAc (40 g). The mixture was heated with stirring at about 140 ° C. for 2 hr and then cooled to room temperature, filtered, and poured into toluene (100 mL). The toluene solution was washed with 5% sodium hydroxide (50 mL) and then twice with deionized water (2×100 mL). After drying with magnesium sulfate and filtering, it was concentrated by rotary evaporation to yield a red solid. The solid was recrystallized from DMAc/water, filtered, and dried to yield 8FNE (3.9 g, 78.8% yield; m.p. 189-191 ° C.; GC/MS m+ /e 582).

Workup

  1. temperatureThe mixture was heated
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. additionpoured into toluene (100 mL)
  5. washThe toluene solution was washed with 5% sodium hydroxide (50 mL)
  6. dry with materialAfter drying with magnesium sulfate
  7. filtrationfiltering
  8. concentrationit was concentrated by rotary evaporation
  9. customto yield a red solid
  10. customThe solid was recrystallized from DMAc/water
  11. filtrationfiltered
  12. customdried
  13. customto yield 8FNE (3.9 g, 78.8% yield; m.p. 189-191 ° C.; GC/MS m+ /e 582)

Sources & evidence

ORD record
ord-f443cb3f88e1420ebc89a658910067fe
Source dataset
uspto-grants-1992_09
Patent number
US05145936

Reaction notes

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