Benzyl Alcohol → HCID 178511263, compound

Participants

Reaction Steps

Trans-4-(aminomethyl)-cyclohexane carboxylic acid (50 g, 0.318 moles), p-toluenesulfonic acid monhydrate (61.7 g, 0.324 moles), benzyl alcohol (250 mL, 2.4 moles) and 250 mL of toluene were combined and stirred. The mixture was refluxed for 24 hours and the liberated water was removed by means of a Dean-Stark apparatus. A clear solution was obtained after 5 hours of refluxing. The solution was allowed to cool to room temperature whereupon the product crystallized. The mixture was vacuum filtered, washed with ether and dried in a vacuum oven to give 128.12 g (96% yield). Greenstein, J. P. and Winitz, M., "Chemistry of the Amino Acids", Robert E. Krieger Publishing Company, Malabar, Fla., Vol. 2, p942 (1986). 1H NMR (CD3OD) 8 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.

Provenance & Evidence