Reaktion #57261

Reaktionsgleichung

3-bromo-4-methylbenzyl alcohol

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title product

Ausbeute 68.5%

3-bromo-4-methylbenzaldehyde

Ausbeute 68.5%

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to RT
2. 2
   Filtrationfiltered through Celite®
3. 3
   Waschenrinsed with CHCl3
4. 4
   Einengenconcentrated to dryness under vacuum
5. 5
   SonstigePurification by flash chromatography on silica gel (10% EtOAc, hexanes)

Vorschrift

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).

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