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

Participants

Reaction Conditions

Reaction Steps

106.16 g (0.4 mol) of 2,4,6-tris(dimethylaminomethyl)phenol and 13.58 g (0.04 mol) of tetrabutylammonium hydrogen sulfate are placed in 200 ml of toluene in a 750 ml sulfonating flask having an anchor mixer, thermometer, reflux condenser and dropping funnel and at RT 80 g (1.0 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 154.5 g (0.8 mol) of octyl bromide are added in the course of 45 minutes. After a subsequent reaction period of 2 hours the mixture is cooled and filtered, and the filtrate is washed once with 30 ml of H20, dried over MgSO4, filtered and concentrated by evaporation, yielding 137.4 g of 2,4,6-tris(dimethylaminomethyl)phenyloctyl ether in the form of a brown, highly viscous liquid which no longer has an 0H band in the IR spectrum and of which the NMR analysis is in agreement with the said structure.

Provenance & Evidence