Benzyl Alcohol → HCID 178427655, compound

Participants

Reaction Steps

Trans-4-(aminomethyl)-cyclohexane carboxylic acid (50 g (0.318 moles)), p-toluenesulfonic acid (61.7 g (0.324 mmoles)), benzyl alcohol (250 mL; 2.4 moles) and toluene (250 mL) were combined and stirred. The resulting mixture was refluxed for 24 hours and the liberated water was removed azeotropically using 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) of the above-identified product. 1H NMR (CD3OD) δ1.05 (, 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.

Provenance & Evidence