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Sodium Carbonate → 6-(4-Pentylphenyl)-1-chloro-2-naphthol

HRID 11989
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11989
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:12])=[C:7]([OH:13])[CH:6]=[CH:5]2.[CH2:14]([C:19]1[CH:24]=[CH:23][C:22](OB(O)O)=[CH:21][CH:20]=1)[CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.C(O)C.O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:14]([C:19]1[CH:20]=[CH:21][C:22]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([Cl:12])=[C:7]([OH:13])[CH:6]=[CH:5]3)=[CH:23][CH:24]=1)[CH2:15][CH2:16][CH2:17][CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 220481596-Bromo-1-chloronaphthalen-2-olHCID 234509174-Pentylphenylboric acidHCID 86587398Ethanol toluene water

Produkt 1

HCID 592642786-(4-Pentylphenyl)-1-chloro-2-naphtholAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

At first, 55 g of 6-bromo-1-chloro-2-naphthol (S1-2), 12.3 g of 4-pentyl-phenylboric acid (S1-3), 1.0 g of tetrakis(triphenylphosphine) palladium, 13.6 g of sodium carbonate and 100 ml of a mixed solvent of toluene/ethanol/water=3/3/1 were added to a reactor in nitrogen atmosphere and refluxed for 10 hours. The reaction solution was cooled to room temperature, added with toluene, and then washed with 1N HCl(aq) and water, dried over magnesium sulfate and distilled under a reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using toluene as an eluting solvent, and then dried under a reduced pressure to obtain 15 g of 6-(4-pentylphenyl)-1-chloro-2-naphthol (S1-4).

Aufarbeitung

  1. temperaturerefluxed for 10 hours
  2. washwashed with 1N HCl(aq) and water
  3. dry with materialdried over magnesium sulfate
  4. distillationdistilled under a reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography
  7. customdried under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ecfb716693ae4e1b944330ff514b9b38
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07727417B2

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