Diethyl Ether → 1-Phenethylamine

Participants

Reaction Steps

The mother liquors from above were acidified with 167 ml. 1N hydrochloric acid, extracted with 5×125 ml. ethyl acetate, the extracts combined, washed with brine, dried (MgSO4) and the solvent evaporated to obtain 49 g. of residue. This was dissolved in 350 ml. warm ethyl acetate, 22.4 g. l-(-)-alpha-methylbenzylamine added and the solution cooled to room temperature. Ethyl ether, 350 ml. was added and the mixture refrigerated overnight. The precipitated solid was collected by filtration, washed with cold ether and dried in vacuo to obtain 44.0 g. of salt. This was dissolved in 880 ml. ethyl acetate and set aside at room temperature for six hours. Filtration gave 12.4 g., M.P. 139°-140° C. After standing overnight, the mother liquor afforded a second crop, 11.66 g., M.P. 139°-140° C. The optical rotation (in chloroform) for the first crop was [alpha]D -30.9°, and [alpha]D -26.6° for the second crop.

Provenance & Evidence