Benzyl Alcohol → HCID 178427655, compound

Participants

Reaction Steps

Trans-4-(aminomethyl)-cyclohexane carboxylic acid (50 g (0.318Moles)), p-toluenesulfonic acid (61.7 g (0.324Moles)), 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) d 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, 5 H), 7.69 (d, 2H). M.P. 154°-156° C.

Provenance & Evidence