Benzyl Alcohol → HCID 178427655, compound

Participants

Reaction Steps

50 g (0.318 moles) trans-4-(aminomethyl)-cyclohexane carboxylic acid, 61.7 g (0.324 moles) p-toluenesulfonic acid, 250 mL (2.4 moles) benzyl alcohol, and 250 mL toluene were combined and stirred at room temperature. The mixture was refluxed for 24 hours and the liberated water removed azeotropically by means of a Dean and 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). 1H NMR (CD3OD) δ 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, 5H), 7.69 (d, 2H). M.P. 154°-156° C. See, Greenstein and Winitz, Chemistry of the Amino Acids. 2: 942 (1986).

Provenance & Evidence