Hydrochloric Acid → 1-Fluoro-6-propyl-2-naphthol

HRID 992183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 992183
[CH2:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:14])[CH:8]=[CH:7]2)[CH2:2][CH3:3].[F:15]C(F)(F)S([O-])(=O)=O.[Na+].Cl>ClCCl.O>[F:15][C:10]1[C:11]2[C:6](=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:13][CH:12]=2)[CH:7]=[CH:8][C:9]=1[OH:14]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 111481346-Propyl-2-naphtholHCID 23676748Sodium trifluoromethanesulfonate

Produkt 1

HCID 117889411-Fluoro-6-propyl-2-naphtholAusbeute 800,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 20 g of 6-propyl-2-naphthol and 1.8 g of sodium trifluoromethanesulfonate in 80 ml of dichloromethane was added 23.7 g of N,N′-difluoro-2,2′-dipyridinium bistetrafluoroborate. The reaction mixture was then stirred for 8 hours. The reaction solution was then poured in water. To the reaction mixture was then added diluted hydrochloric acid. The resulting organic phase was then separated. The resulting aqueous phase was extracted with toluene. The organic phase and the material thus extracted were together washed sequentially with water and saturated brine, and then dehydrated and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain an oily matter which was then purified through silica gel column chromatography (hexane/ethyl acetate=9/1) to obtain 17.1 g of 1-fluoro-6-propyl-2-naphthol.

Aufarbeitung

  1. customThe resulting organic phase was then separated
  2. extractionThe resulting aqueous phase was extracted with toluene
  3. extractionThe organic phase and the material thus extracted
  4. washwere together washed sequentially with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customto obtain an oily matter which
  8. customwas then purified through silica gel column chromatography (hexane/ethyl acetate=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-fe9e0807aa1e41c791ab4edebc2636fc
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06468607B1

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