Benzyl Alcohol → HCID 178427655, compound

Participants

Reaction Steps

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.

Provenance & Evidence