Reaktion #744647

Reaktionsgleichung

2-nitrobenzyl alcohol

11-bromoundecanoic acid

DCC

→

2-nitrobenzyl 11-bromoundecanoate

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONUpon addition a yellow-brown precipitate
2. 2
   Sonstigeformed after a few minutes
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature overnight
4. 4
   SonstigeThe precipitate was removed by vacuum filtration
5. 5
   Sonstigethe solvent was removed by rotovap
6. 6
   SonstigeThe product was purified
7. 7
   TrocknenThe product was dried over Na2SO4
8. 8
   Sonstigethe solvent removed by rotovap
9. 9
   Sonstigedried under vacuum
10. 10
    Sonstigeproducing a white solid

Vorschrift

One equivalent of 2-nitrobenzyl alcohol (1.91 g, 12.49 mmol) was combined with one equivalent of 11-bromoundecanoic acid (3.31 g, 12.49 mmol), 0.1 equivalents DMAP (0.153 g, 1.25 mmol) and dissolved in 100 mL CH2Cl2. To this mixture a solution of DCC (2.58 g, 12.49 mmol) in 50 mL CH2Cl2 was slowly added while stirring. Upon addition a yellow-brown precipitate formed after a few minutes. The mixture was stirred at room temperature overnight. The precipitate was removed by vacuum filtration and the solvent was removed by rotovap. The product was purified using silica gel column chromatography with CH2Cl2/MeOH (v/v 50:1) as eluent. The product was dried over Na2SO4, the solvent removed by rotovap, and dried under vacuum, producing a white solid. Yield: 4.37 g (87.4%). 1H-NMR (CDCl3) δ (ppm): 8.1 (d, 1H, Ar), 7.6 (t, 1H, Ar), 7.5 (d, 1H, Ar), 7.4 (t, 1H, Ar), 5.5 (s, 2H, O—CH2), 3.4 (t, 2H, CH2—Br), 2.4 (t, 2H, CH2—C═O), 1.8 (m, 2H, CH2), 1.6 (m, 2H, CH2), 1.4 (m, 2H, CH2), 1.3 (m, 10H, CH2). 13C-NMR (CDCl3) δ (ppm): 173.5, 147.9, 134.1, 132.7, 129.5, 129.2, 125.5, 63.2, 34.6, 34.5, 33.2, 29.7, 29.6, 29.5, 29.4, 29.1, 28.5, 25.3.

Quelle