2,4,6-Tris((dimethylamino)methyl)phenol → 2,4,6-Tris(dimethylaminomethyl)phenylbutyl ether

Participants

Reaction Conditions

Reaction Steps

53.1 g (0.2 mol) of 2,4,6-tris(dimethylaminomethyl)phenol and 6.8 g (0.02 mol) of tetrabutylammonium hydrogen sulfate are placed in 100 ml of toluene in a 350 ml sulfonating flask having an anchor mixer, thermometer, reflux condenser and dropping funnel and at RT 40 g (0.5 tool) of a 50% aqueous NaOH solution are added dropwise in the course of 30 minutes. The suspension is then stirred for 30 minutes at 80° C. and then at the same temperature 54.8 g (0.4 mol) of butyl bromide are added in the course of 45 minutes. After a subsequent reaction period of 3 hours the mixture is cooled and filtered, and the filtrate is washed once with 30 ml of H2O, dried over MgSO4, filtered and concentrated by evaporation, yielding 48 g of 2,4,6-tris(dimethylaminomethyl)phenylbutyl ether in the form of a brown liquid which no longer has an OH band in the IR spectrum and of which the NMR analysis is in agreement with the said structure.

Provenance & Evidence