1-Naphthol → 1,4-Bis(1-naphthoxy)tetrafluorobenzene

HRID 1031052

Reaction equation

F[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5](F)=[C:4]([F:11])[C:3]=1[F:12].[C:13]1([OH:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[C:13]1([O:23][C:2]2[C:3]([F:12])=[C:4]([F:11])[C:5]([O:27][C:24]3[C:22]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:18]=[CH:19][CH:20]=3)=[C:6]([F:9])[C:7]=2[F:8])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 140 °C

Procedure

The monomer 1,4-bis(1-naphthoxy)tetrafluorobenzene (4FNE) was prepared as follows. A 100 mL round bottom flask equipped with a magnetic stirrer was charged with hexafluorobenzene (3.53 g, 0.0190 mole), 1-naphthol, and DMAc (50 mL). After the solids dissolved, potassium carbonate (6.50 g, 0.048 mole) was added and the mixture was heated at about 140° C. for 2 hr. The mixture was then cooled to room temperature, filtered, and poured into toluene (150 mL). The toluene solution was washed twice with water (2×150 mL) and concentrated by rotary evaporation to yield an off-white powder (7.91 g). Analysis of the powder by GC showed a mixture of isomers (2% ortho, 8% meta, and 90% para). The powder was recrystallized from a mixture of N,N-dimethylformamide (DMF) and water to yield the desired all-para 4FNE, GC/MS (m+ /e 434).

Workup

customA 100 mL round bottom flask equipped with a magnetic stirrer
dissolutionAfter the solids dissolved
temperatureThe mixture was then cooled to room temperature
filtrationfiltered
additionpoured into toluene (150 mL)
washThe toluene solution was washed twice with water (2×150 mL)
concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record: ord-e6d43dddf9544c719bdb39274ca9741e
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05108840

Linked notes

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