3-Hydroxybenzaldehyde → 3-(4-Methylphenoxy)benzaldehyde

HRID 1678581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678581
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 1013-HydroxybenzaldehydeHCID 8471TriethylamineHCID 79799Tolylboronic acid

Produkt 1

HCID 6113073-(4-Methylphenoxy)benzaldehydeAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Hydroxybenzaldehyde (1.0 g, 8.2 mmol) was dissolved in dichloromethane (50 mL). (4-Methylphenyl)boronic acid (2.2 g, 16.4 mmol), triethylamine (5.7 mL, 41.0 mmol) and copper acetate(II) (1.5 g, 8.2 mmol) were added thereto, and then the mixture was stirred at room temperature for 2 days. The reaction solution was filtered, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30) to give the title compound (324 mg, yield 19%).

Aufarbeitung

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-435bf42d60454fdf8ca49b3d94b55299
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008525B2

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