Benzyl Bromide → HCID 22127020, Verbindung

HRID 872023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872023
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:17]=1>C(#N)C.C(OCC)(=O)C>[CH2:7]([O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13080945Ethyl 4-hydroxynaphthalene-2-carboxylate

Produkt 1

HCID 22127020HCID 22127020, VerbindungAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium carbonate (19.2 g) and benzyl bromide (19.0 g) were added to a solution of ethyl 4-hydroxy-2-naphthoate (20 g) in acetonitrile (200 ml) and the mixture was heated to reflux for 2 hours. After being cooled, the reaction solution was diluted with ethyl acetate and insoluble materials were filtered through Celite. The filtrate was concentrated in vacuo and the resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=100/1) to give ethyl 4-(benzyloxy)-2-naphthoate (27.8 g) as a pale yellow oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter being cooled
  4. filtrationwere filtered through Celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=100/1)

Quellen und Nachweise

ORD-Eintrag
ord-36d45e44faa84bc589afe7bec1b08f06
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975252B2

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