4-(2-Amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol → N-[2-(4-Hydroxymethylphenyl)-1-methylethyl]-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethanamine

Participants

Reaction Steps

A mixture of 1-(4-hydroxymethylphenyl)propan-2-one (1.64 g) and 2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl) ethanamine (1.23 g) in ethanol (80 ml) was refluxed 0.5 hours, cooled to ambient temperature, platinum oxide (0.1 g) added and the mixture hydrogenated at 75 psi and 50°-60° for 8 hours. The solution was filtered, evaporated, the residue taken up in ethyl acetate and filtered again. Removal of the solvent gave the title compound as an oil which was finally obtained as a hard foam, (52:48 mixture of diastereoisomers) from ethyl acetate-benzene.

Provenance & Evidence