反应 #351186

反应方程式

trans-4-(aminomethyl)-cyclohexane carboxylic acid

p-toluenesulfonic acid

benzyl alcohol

→

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

收率 96.0%

溶剂

toluene

反应条件

后处理

1. 1
   温度The mixture was refluxed for 24 hours
2. 2
   其他the liberated water was removed azeotropically by means of a Dean-Stark apparatus
3. 3
   其他A clear solution was obtained after 5 hours
4. 4
   温度of refluxing
5. 5
   其他the product crystallized
6. 6
   过滤filtered
7. 7
   洗涤washed with ether
8. 8
   其他dried in a vacuum oven
9. 9
   其他to give 128.12 g (96% yield.)

实验过程

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.

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