Tert-Butylamine → 2-Chloro-α-[[(1,1-dimethylethyl)amino]methyl]-5-hydroxybenzenemethanol

Participants

Reaction Steps

To a solution of 2-chloro-5-hydroxyphenylglyoxal (1.85 g) in methanol (37 ml) was added a solution of tert-butylamine (3.65 g) in methanol under cooling, further the sodium borohydride (0.57 g) was added in small portions, and the reaction mixture was stirred for 3 hours. The reaction mixture was evaporated and the residue acidified with 10% HCl, and washed with ether. The aqueous layer was made alkaline with K2CO3, and extracted with ether. The extract was dried with Na2SO4 and evaporated. The residue was recrystallized from iso-propylether n-hexane to give a 2-chloro-5-hydroxy-α-(tert-butylaminomethyl)-benzylalcohol, m.p. 162° - 163° C. Hydrochloride: m.p. 245° - 248° C.

Provenance & Evidence