Реакция #948751

Уравнение реакции

trans-4-(aminomethyl)-cyclohexane carboxylic acid

p-toluenesulfonic acid

benzyl alcohol

→

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

Выход 96.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was refluxed for 24 hours
2. 2
   Другоеthe liberated water removed azeotropically by means of a Dean and Stark apparatus
3. 3
   ДругоеA clear solution was obtained after 5 hours
4. 4
   Температураof refluxing
5. 5
   Температураto cool to room temperature
6. 6
   Другоеthe product crystallized
7. 7
   Фильтрацияfiltered
8. 8
   Промывкаwashed with ether
9. 9
   Другоеdried in a vacuum oven
10. 10
    Другоеto give 128.12 g (96% yield)

Методика

50 g (0.318 moles) 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 at room temperature. The mixture was refluxed for 24 hours and the liberated water removed azeotropically by means of a Dean and 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). 1H NMR (CD3OD) δ 1.05 (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. See, Greenstein and Winitz, Chemistry of the Amino Acids. 2: 942 (1986).

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