反应详情

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.

1. temperaturewas heated
2. temperatureto reflux under a N2 atmosphere
3. customto collect water
4. customformed during the reaction
5. temperatureDuring reflux
6. dissolutionall solids dissolved
7. customto leave a colorless solution
8. temperatureAfter 3 hours at reflux
9. temperatureHeat
10. customwas removed
11. customThe solids which separated out
12. customwere collected
13. washwashed with diethyl ether