Hydrogen Bromide → 1-Hydroxy-5-phenoxynaphthalene

HRID 2288907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2288907
C[O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 187020411-Methoxy-5-phenoxynaphthalene

Produkt 1

HCID 187020401-Hydroxy-5-phenoxynaphthaleneAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
97.5 °C

Versuchsvorschrift

Into 50 mL of glacial acetic acid, 3.7 g of 1-methoxy-5-phenoxynaphthalene prepared as above, followed by 20 mL of 40% aqueous hydrogen bromide was stirred. The mixture was heated at 95-100° C. for 16 hours. The solvent was removed under vacuum, and the residue was redissolved in ethyl acetate and washed three times with brine. The organic layer was dried over magnesium sulfate and filtered. After removing solvent, the residue was chromatographed over silica gel with a gradient elution of 0 to 30% ethyl acetate in hexane, providing 2.10 g (59%) of 1-hydroxy-5-phenoxynaphthalene.

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was redissolved in ethyl acetate
  3. washwashed three times with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customAfter removing solvent
  7. customthe residue was chromatographed over silica gel with a gradient elution of 0 to 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-d1b49b4548f74fc59f1de55bc3c97665
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06090850

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