반응 #9006

반응 방정식

methyl 4-(bromomethyl)benzoate

sodium cyanide

→

4-cyanomethyl-benzoic acid methyl ester

수율 60.1%

용매

benzene water

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 5 h
3. 3
   추출then extracted with CH2Cl2 3×50 mL)
4. 4
   건조The organic extracts were dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification of the crude material by chromatography on silica gel (35% EtOAc/hexanes)

실험 절차

A mixture of methyl 4-(bromomethyl)benzoate (10.09 g, 44.05 mmol), sodium cyanide (6.42 g, 131 mmol) and cetyltrimethylammonium bromide (1.59 g, 4.36 mmol) in benzene/water (2:1, 187.5 mL) was heated at reflux for 5 h then extracted with CH2Cl2 3×50 mL). The organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. Purification of the crude material by chromatography on silica gel (35% EtOAc/hexanes) gave 4-cyanomethyl-benzoic acid methyl ester as a colourless solid (4.64 g, 60%). 1H NMR (CDCl3) δ 3.82 (s, 2H), 3.93 (s, 3H), 7.42 (d, 2H, J=9 Hz), 8.06 (d, 2H, J=9 Hz).

출처