Reaktion #75878

Reaktionsgleichung

1-cyclopentyloxy-2-methoxy-5-nitrobenzene

→

3-cyclopentyloxy-4-methoxyaniline

Ausbeute 95.4%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was degassed under vacuum three times
2. 2
   FiltrationThe reaction mixture was filtered through a pad of celite
3. 3
   Waschenthe celite was rinsed with additional ethanol
4. 4
   SonstigeThe solvent was removed in-vacuo

Vorschrift

To a suspension of 10% Pd on activated carbon (25 g) in ethanol (4L), under N2 protection, was added 1-cyclopentyloxy-2-methoxy-5-nitrobenzene (250 g, 1.054 mol). The reaction mixture was degassed under vacuum three times. The reaction mixture was stirred vigorously while hydrogen gas was allowed to flow over the reaction mixture. After 4 h the reaction was complete by TLC (5:1 hex:EA). The reaction mixture was filtered through a pad of celite and the celite was rinsed with additional ethanol. The solvent was removed in-vacuo to obtain 208.38 g (95% yield) of 3-cyclopentyloxy-4-methoxyaniline as a red liquid. 1H NMR (CDCl3) δ 6.85 (d. J=8.4 Hz, 1H), 6.29 (s, 1H), 6.19 (dd, J=2.8, 8.4, 1H), 4.69 (p, J=4.4 Hz, 1H), 3.75 (s, 3H), 3.44 (bs, 2H),1.90-1.81 (m, 6H), 1.61-1.55 (m, 2H).

Quelle