(3-Bromo-4-methylphenyl)methanol → 3-Bromo-4-methylbenzaldehyde

HRID 28983

Reaktionsgleichung

Reaktionsgleichung von HRID 28983
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH2:5][OH:6]>C(Cl)(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=[O:6]

Komponenten

4

Edukt 1

HCID 12947381(3-Bromo-4-methylphenyl)methanol

Produkt 1

HCID 8167653-Bromo-4-methylbenzaldehydeAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirred solution of 3-bromo-4-methylbenzyl alcohol (4.43 g, 22 mMol) in CHCl3 (100 mL) was added MnO2 (15 g, 172 mMol). The reaction was stirred and refluxed (70° C. oil bath) for 18 h, cooled to RT, filtered through Celite®, rinsed with CHCl3, and concentrated to dryness under vacuum. Purification by flash chromatography on silica gel (10% EtOAc, hexanes) gave the title product (3.0 g, 68%). 1H NMR (400 MHz, CDCl3) δ 9.98 (s, 1H), 7.75 (d, J=1.5 Hz, 1 H), 7.73 (d, J=8.1 Hz, 1 H), 7.57 (dd, J=8.1, 1.5 Hz, 1 H), 7.28 (s, 1 H), 2.50 (s, 3 H).

Aufarbeitung

  1. temperaturecooled to RT
  2. filtrationfiltered through Celite®
  3. washrinsed with CHCl3
  4. concentrationconcentrated to dryness under vacuum
  5. customPurification by flash chromatography on silica gel (10% EtOAc, hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f78c4646b15c4012aec48bbca2c189b1
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419988B2

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