Реакция #950586

Уравнение реакции

trans-4-aminomethylcyclohexane-1-carboxylic acid

4-toluenesulfonic acid

benzyl alcohol

→

product

Выход 92.0%

Benzyl trans-4-aminomethylcyclohexane-1-carboxylate-p-toluenesulfonic acid salt

Выход 92.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураto reflux under a N2 atmosphere
3. 3
   Другоеto collect water
4. 4
   Другоеformed during the reaction
5. 5
   ТемператураDuring reflux
6. 6
   workup.DISSOLUTIONall solids dissolved
7. 7
   Другоеto leave a colorless solution
8. 8
   ТемператураAfter 3 hours at reflux
9. 9
   ТемператураHeat
10. 10
    Другоеwas removed
11. 11
    ДругоеThe solids which separated out
12. 12
    Другоеwere collected
13. 13
    Промывкаwashed with diethyl ether

Методика

A mixture of 10.0 g (63.6 mmol) of trans-4-aminomethylcyclohexane-1-carboxylic acid, 25.1 g (132 mmol) of 4-toluenesulfonic acid, 50 mL (482 mmol) of benzyl alcohol, and 75 mL of toluene was heated to reflux under a N2 atmosphere using a Dean-Stark trap to collect water formed during the reaction. During reflux, all solids dissolved to leave a colorless solution. After 3 hours at reflux, the solution began to turn yellow. Heat was removed, and the flask allowed to cool to room temperature. The solids which separated out were collected and washed with diethyl ether. There was obtained 24.5 g (58.4 mmol, 92% yield) of product as a white solid. NMR (CD3OD): 7.12/7.20/7.65/7.73 (ABq, C6H4); 7.26 (s, C6H5); 5.06 (s, OCH2 C6H5); 2.72/2.80 (d, CH2N); 2.32 (s, ArCH3); 1.00-2.18 (m, cyclohexyl H). MS: M+ =247 by electron-impact; calculated M+ =247.3.

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