تفاعل #351186

معادلة التفاعل

trans-4-(aminomethyl)-cyclohexane carboxylic acid

p-toluenesulfonic acid

benzyl alcohol

→

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

المردود 96.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was refluxed for 24 hours
2. 2
   أخرىthe liberated water was removed azeotropically by means of a Dean-Stark apparatus
3. 3
   أخرىA clear solution was obtained after 5 hours
4. 4
   درجة الحرارةof refluxing
5. 5
   أخرىthe product crystallized
6. 6
   ترشيحfiltered
7. 7
   غسيلwashed with ether
8. 8
   أخرىdried in a vacuum oven
9. 9
   أخرىto give 128.12 g (96% yield.)

الإجراء التجريبي

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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