Reaktion #351186

Reaktionsgleichung

trans-4-(aminomethyl)-cyclohexane carboxylic acid

p-toluenesulfonic acid

benzyl alcohol

→

trans-4-(aminomethyl)-cyclohexane carboxylic acid benzyl ester para-toluenesulfonate salt

Ausbeute 96.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 24 hours
2. 2
   Sonstigethe liberated water was removed azeotropically by means of a Dean-Stark apparatus
3. 3
   SonstigeA clear solution was obtained after 5 hours
4. 4
   Temperaturof refluxing
5. 5
   Sonstigethe product crystallized
6. 6
   Filtrationfiltered
7. 7
   Waschenwashed with ether
8. 8
   Sonstigedried in a vacuum oven
9. 9
   Sonstigeto give 128.12 g (96% yield.)

Vorschrift

50 g (0.318 moles) of trans-4-(aminomethyl)-cyclohexane carboxylic acid, 61.7 g (0.324 moles) p-toluenesulfonic acid, 250 mL (2.4 moles) benzyl alcohol and 250 mL toluene were combined and stirred. The mixture was refluxed for 24 hours and the liberated water was removed azeotropically by means of a Dean-Stark apparatus. A clear solution was obtained after 5 hours of refluxing. The solution was allowed to cool to room temperature and the product crystallized. The mixture was vacuum filtered, washed with ether and dried in a vacuum oven to give 128.12 g (96% yield.). Reference: Greenstein, Jesse P.; Winitz, Milton. Chemistry of the Amino Acids. vol. 2, (1986), 942. 1H NMR (CD3OD) δ1.05 (m, 2H), 1.43 (m, 2H), 1.59 (m, 1H), 1.85 (m, 2H), 2.03 (m, 2H), 2.33 (m, 1H), 2.35 (s, 3H), 2.75 (d, 2H), 5.09 (s, 2H), 7.23 (d, 2H), 7.32 (m, 5H), 7.69 (d, 2H). M.P. 154°-156 C.

Quelle