16934-77-3Relevant articles and documents
Demailly,Solladie
, p. 1885 (1977)
Menthylamine synthesis via gold-catalyzed hydrogenation of menthone oxime
Demidova, Yu. S.,Mozhaitsev, E. S.,Murzin, D. Yu.,Nefedov, A. A.,Salakhutdinov, N. F.,Saraev, A. A.,Simakov, A.,Simakova, I. L.,Suslov, E. V.,Volcho, K. P.
, (2020/09/03)
In the current work gold nanoparticles supported on oxides (MgO, Al2O3, ZrO2, TiO2) were used for menthylamine synthesis via menthone oxime hydrogenation. An increase of the gold nanoparticles size and application of metal oxides with a strong basic character such as magnesia favored deoximation to menthone. Au/Al2O3 catalyst with the gold nanoparticles size of 2.0 nm afforded high catalytic activity and selectivity to menthylamine. The reaction kinetics including stereoselectivity to the reaction products and recyclability of the catalyst was studied using Au/Al2O3 in the temperature range 90?110 °C under hydrogen pressure of 5.5–7.5 bar. The catalytic behavior was influenced by the solvent nature, with higher selectivity to desired amine achieved using methanol. The reaction rate was pressure independent, while has first order with respect to menthone oxime concentration. Stereoselectivity to menthylamines and menthones was independent on the reaction temperature and the hydrogen pressure.
Practical synthesis of optically pure menthylamines starting from racemic neomenthol
Welschoff, Nina,Waldvogel, Siegfried R.
experimental part, p. 3596 - 3601 (2010/12/19)
A reliable and scalable route to racemic and highly enantiomerically enriched menthylamines exploits the technical product rac-neomenthol as the starting material. The elaborated protocol is based on nucleophilic substitution of the hydroxy moiety by azide. Subsequent reduction and resolution with tartaric acid provides the desired optically enriched menthylamines.
