Reaktion #9007

Reaktionsgleichung

alcohol

[2-(4-Hydroxymethyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

→

aldehyde

Ausbeute 88.0%

[2-(4-Formyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

Ausbeute 88.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through Celite
2. 2
   Waschenthe cake was washed with CH2Cl2
3. 3
   SonstigeThe solvent was removed from the filtrate under reduced pressure

Vorschrift

To a solution of the alcohol from above (200 mg, 0.796 mmol) in CH2Cl2 (8 mL) was added activated MnO2 (814 mg, 7.96 mmol) and the mixture stirred at room temperature for 69 h. The reaction mixture was filtered through Celite and the cake was washed with CH2Cl2. The solvent was removed from the filtrate under reduced pressure to give the desired aldehyde as colourless crystals (175 mg, 88%). 1H NMR (CDCl3) δ 1.43 (s, 9H), 2.89 (m, 2H), 3.41 (m, 2H), 4.55 (br s, 1H), 7.37 (d, 2H, J=8.1 Hz), 7.83 (d, 2H, J=7.8 Hz), 9.99 (s, 1H).

Quelle